Cinnamoyl derivatives and use thereof

ABSTRACT

The present invention relates to a cinnamoyl compound represented by the formula (I):

This application is a U.S. national stage of International ApplicationNo. PCT/JP2004/013989 filed Sep. 16, 2004.

TECHNICAL FIELD

The present invention relates to cinnamoyl derivatives use thereof.

BACKGROUND ART

In diseases and disorders such as hepatic cirrhosis, interstitialpulmonary disease, chronic renal failure (or disease resulting inchronic renal failure), hyperplasia scar after inflammation,postoperative scars or burn scars, scleroderma, arteriosclerosis,hypertension and the like, excessive accumulation of an extracellularmatrix, a representative of which is collagen, causes fibrosis andsclerosis of tissues, resulting in decreased functions, cicatrizationand the like in the organs or tissues. Such excessive accumulation of anextracellular matrix is induced by increased production of collagen dueto a breakdown of balance between biosynthesis and degradation ofcollagen and the like. In fact, it has been observed that expression ofa collagen gene, in particular, a Type I collagen gene has beenincreased in a fibrotic tissue [e.g. J. Invest. Dermatol., 94, 365,(1990) and Proc. Natl. Acad. Sci. USA, 88, 6642, (1991)]. It has beenalso observed that the amount of TGF-β, which is a cytokine, has beenincreased in a fibrotic tissue [e.g. J. Invest. Dermatol., 94, 365,(1990) and Proc. Natl. Acad. Sci. USA, 88, 6642, (1991)]. It has beenshown that TGF-β has increased expression of a Type I collagen gene andbeen involved in increased production of collagen and, consequently,fibrosis of a tissue [e.g. Lab. Invest., 63, 171, (1990) and J. Invest.Dermatol., 94, 365, (1990)]. It has been also shown that byadministering an anti-TGF-β antibody or a soluble anti-TGF-β receptor toa model animal of tissue fibrosis, improvement of tissue fibrosis hasbeen achieved and thereby the tissue function has been also improved[e.g. Diabetes, 45, 522-530, (1996), Proc. Natl. Acad. Sci. USA, 96,12719-12724, (1999) and Proc. Natl. Acad. Sci. USA, 97, 8015-8020,(2000)]. It has been also known that by administering a compound whichsuppressively acts on intracellular signal transduction via TGF-β,improvement in fibrosis of a tissue has been achieved and thereby thetissue function has been also improved [e.g. Autoimmunity, 35, 277-282,(2002), J. Hepatol., 37, 331-339, (2002) and Life Sci., 71, 1559-1606,(2002)].

Thus, there is a need for development and provision of a drug whichimproves fibrosis of a tissue by decreasing expression of a Type Icollagen gene in the tissue to reduce accumulation of collagen (i.e. acollagen accumulation-suppressing agent and a fibrosing disease-treatingagent).

DISCLOSURE OF THE INVENTION

Under these circumstances, the present inventors have intensivelystudied and, as a result, found out that compounds represented by thefollowing formulas (I) to (V), (VII), (VIII), (X), (XI), (XIII), and(XV) to (XIV) has the ability to suppress transcription of I typecollagen gene. Thus, the present invention has been completed.

That is, the present invention provides:

1. A I type collagen gene transcription suppressing composition, whichcomprises a cinnamoyl compound represented by the formula (I):

[wherein

-   I. A represents a benzene ring or a pyridine ring, in (Y_(α))_(q),    Y_(α) is a substituent on a carbon atom, and represents a    substituent of the following X₀ group or Y₀ group, q represents 0,    1, 2, 3, 4 or 5, when q is 2 or more, Y_(α)'s are the same or    different and, when q is 2 or more, the adjacent two same or    different Y_(α)'s constitute a group of a Z₀ group, and may be fused    with an A ring;-   (1) a X₀ group:-   a M_(a)-group [M_(a) represents a R_(b)-group (R_(b) represents a    C1-C10 alkyl group optionally substituted with a halogen atom), a    halogen atom, a nitro group, a cyano group, a hydroxy group, a    R_(c)—B_(a)—R_(d)-group (R_(c) represents a C1-C10 alkyl group    optionally substituted with a halogen atom, B_(a) represents an oxy    group, a thio group, a sulfinyl group or a sulfonyl group, R_(d)    represents a single bond or a C1-C10 alkylene group), a    HOR_(d)-group (R_(d) is as defined above), a R_(e)—CO—R_(d)-group    (R_(e) represents a hydrogen atom, or a C1-C10 alkyl group    optionally substituted with a halogen atom, and R_(d) is as defined    above), a R_(e)—CO—O—R_(d)-group (R_(e) and R_(d) are as defined    above), a R_(e)O—CO—R_(d)-group (R_(e) and R_(d) are as defined    above), a HO—CO—CH═CH-group, a R_(e)R_(e)′N—R_(d)-group (R_(e) and    R_(e)′ are the same or different, R_(e) is as defined above, R_(e)′    has the same meaning as that of R_(e), and R_(d) is as defined    above), a R_(b)O—CO—NR_(e)′—R_(d)-group (R_(b), R_(e)′ and R_(d) are    as defined above), a R_(b)O—CO—N(R_(e))—R_(d)-group (R_(b), R_(e)    and R_(d) are as defined above), a R_(e)R_(e)′N—CO—R_(d)-group    (R_(e), R_(e)′ and R_(d) are as defined above), a    R_(e)R_(e)′N—CO—NR_(e)″—R_(d)-group (R_(e), R_(e)′ and R_(e)″ are    the same or different, R_(e) and R_(e)′ are as defined above, R_(e)″    has the same meaning as that of R_(e), and R_(d) is as defined    above), a R_(e)R_(e)′N—C(═NR_(e)″)—R_(e)′″—R_(d)-group (R_(e),    R_(e)′, R_(e)″ and R_(e)′″ are the same or different, R_(e), R_(e)′    and R_(e)″ are as defined above, R_(e)′″ has the same meaning as    that of R_(e), and R_(d) is as defined above), a    R_(b)—SO₂—NR_(e)—R_(d)-group (R_(b), R_(e) and R_(d) are as defined    above), a R_(e)R_(e)′N—SO₂—R_(d)-group (R_(e), R_(e)′ and R_(d) are    as defined above), a C2-C10 alkenyl group or a C2-C10 alkynyl    group.];-   (2) a Y₀ group:

a M_(b0)-R_(d)-group [M_(b0) represents a M_(c0)-group {M_(c0)represents a M_(d0)-R_(d)′-group {M_(d0) represents a 6 to 10-memberedaryl group optionally substituted with a M_(a)-group (M_(a) is asdefined above), or 5 to 10-membered heteroaryl group optionallysubstituted with M_(a) group (M_(a) is as defined above), or a 3 to10-membered hydrocarbon ring or heterocycle optionally substituted witha M_(a)-group (M_(a) is defined above) and optionally containing anunsaturated bond, or

a (b₀)-group (in (b₀), G₀ constitutes a saturated or unsaturatednon-aromatic 5 to 14-membered hydrocarbon ring or heterocycle optionallyhaving a substituent),

a (c₀)-group (in (C₀), J₀ may contain a nitrogen atom, and constitutesan aromatic 5 to 7-membered ring),

a (d₀)-group {d₀ represents a 5 to 12-membered hydrocarbon ringsubstituted with carbonyl group or a thiocarbonyl group and, further,optionally substituted with an oxy group, a thio group, a —NR₁-group {R₁represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10 alkylgroup substituted with halogen atom or a R₂—B₁-group (R₂ represents aC1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10 alkenyl group,and B₁ represents an oxy group, a thio group, a sulfinyl group or asulfonyl group), or a C3-C10 alkenyl group, or a C3-C10 alkenyl group},a sulfinyl group, or a sulfonyl group} or

an (e₀)-group {e₀ constitutes a 5 to 12-membered hydrocarbon ringoptionally substituted with a carbonyl group, a thiocarbonyl group, anoxy group, a thio group, a —NR₁-group (R₁ is as defined above), asulfinyl group or a sulfonyl group}, R_(d)′ is the same as or differentfrom R_(d), and has the same meaning as that of R_(d)}}, aM_(c0)-B_(a)-group (M_(c0) and B_(a) are as defined above), aM_(c0)-CO-group (M_(c0) is as defined above), a M_(c0)-CO—O group(M_(c0) is as defined above), a M_(c0)O—CO-group (M_(c0) is as definedabove), a M_(c0)R_(e)N-group (M_(c0) and R_(e) are as defined above), aM_(c0)-CO—NR_(e)-group (M_(c0) and R_(e) are as defined above), aM_(c0)O—CO—NR_(e)-group (M_(c0) and R_(e) are as defined above), aM_(c0)R_(e)N—CO-group (M_(c0) and R_(e) are as defined above), aM_(c0)R_(e)N—CO—NR_(e)′-group (M_(c0), R_(e) and R_(e)′ are as definedabove), a M_(c0)R_(e)N—C(═NR_(e)′)—NR_(e)″-group (M_(c0), R_(e), R_(e)′and R_(e)″ are as defined above), a M_(c0)-SO₂—NR_(e)-group (M_(c0) andR_(e) are as defined above) or M_(c0)R_(e)N—SO₂-group (M_(c0) and R_(e)are as defined above), and R_(d) is as defined above.];

-   (3) a Z₀ group: a group which is a 5 to 12-membered hydrocarbon ring    or heterocycle having a halogen atom, a C1-C10 alkoxy group, a    C3-C10 alkenyloxy group, a C3-C10 alkynyloxy group, a carbonyl    group, a thiocarbonyl group, an oxy group, a thio group, a sulfinyl    group or a sulfonyl group, is an aromatic or non-aromatic monocyclic    or fused ring, and is fused with an A ring;-   II. Q_(α) represents an optionally substituted hydroxyl group, or an    optionally substituted amino group;-   III. W_(α) represents an oxygen atom or a-NT_(α)-group (T_(α)    represents a hydrogen atom, or a substituent on a nitrogen atom.);-   IV. K_(α) and L_(α) are the same or different, and represent a    hydrogen atom, or a substituent on a carbon atom, or K_(α) and L_(α)    may form a C1-C10 alkylene group optionally having a substituent or    a C1-C10 alkenylene group optionally having a substituent; provided    that when an A ring is a benzene ring, W_(α) is an oxygen atom,    L_(a) is a methyl group, K_(α) is a hydrogen atom, and Q_(α) is a    C1-C4 alkoxy group, a C3-C4 alkenyloxy group or a C3-C4 alkynyloxy    group, then q is not 0 and, when an A ring is a benzene ring, W_(α)    is an oxygen atom, L_(α) is a methyl group, K_(α) is a hydrogen    atom, and Q_(α) is a C1-C4 alkoxy group, a C3-C4 alkenyloxy group or    a C3-C4 alkynyloxy group, then q is 1, and Y_(α) is not a halogen    atom, or a C1-C4 alkyl group optionally substituted with a halogen    atom or a C1-C4 alkoxy group, or a nitro group, or a C1-C4 alkoxy    group, or a RB-group (R represents a C1-C4 haloalkyl group, and B    represents an oxy group or a thio group) and, when A is a benzene    ring, W_(α) is an oxygen atom, L_(α) and K_(α) form a    1,3-butadienylene group, and Q_(α) is a methoxy group, then q is 1,    and Y_(α) is not a methoxy group or an ethoxy group and, when A is a    benzene ring, W_(α) is an oxygen atom, L_(α) and K_(α) form a    1,3-butadienylene group, and Q_(α) is a hydroxyl group, then q is 1,    and Y_(α) is not an ethoxy group; and

the “as defined above” in the same symbol between a plurality ofsubstituents indicates that the plurality of substituents independentlyrepresent the same meaning as that described above and, between theplurality of substituents, a selection range of selected substituents isthe same, while the selected substituents may be the same or thedifferent as far as they are selected in the range]; and an inertcarrier;

2. A I type collagen gene transcription suppressing composition, whichcomprises a cinnamoyl compound represented by the formula (II):

[wherein

-   I. A represents a benzene ring or pyridine ring;-   II. In (Y_(A0))q, Y_(A0) is a substituent on a carbon atom, and    represents a substituent of the following X₀ group and Y₀ group, q    represents 0, 1, 2, 3, 4 or 5, when q is 2 or more, Y_(A0)'s are the    same or different and, when q is 2 or more, the adjacent two same or    different Y_(A0)'s constitute a group of a Z₀ group, and may be    fused with an A ring;-   (1) a X₀ group:

a M_(a)-group [M_(a) represents a R_(b) group (R_(b) represents a C1-C10alkyl group optionally substituted with a halogen atom), a halogen atom,a nitro group, a cyano group, a hydroxyl group, aR_(c)—B_(a)—R_(d)-group (R_(c) represents a C1-C10 alkyl groupoptionally substituted with a halogen atom, B_(a) represents an oxygroup, a thio group, a sulfinyl group or a sulfonyl group, and R_(d)represents a single bond or a C1-C10 alkylene group), a HOR_(d)-group(R_(d) is as defined above), a R_(e)—CO—R_(d)-group (R_(e) representshydrogen atom, or a C1-C10 alkyl group optionally substituted with ahalogen atom, and R_(d) is as defined above), a R_(e)—CO—O—R_(d)-group(R_(e) and R_(d) are as defined above), a R_(e)O—CO—R_(d)-group (R_(e)and R_(d) are as defined above), a HO—CO—CH═CH-group, aR_(e)R_(e)′N—R_(d)-group (R_(e) and R_(e)′ are the same or different,R_(e)′ has the same meaning as that of R_(e) and R_(d) is as definedabove), a R_(e)—CO—NR_(e)′—R_(d)-group (R_(e), R_(e)′ and R_(d) are asdefined above), a R_(b)C—CO—N(R_(e))—R_(d)-group (R_(b), R_(e) and R_(d)are as defined above), a R_(e)R_(e)′N—CO—R_(d)-group (R_(e), R_(e)′ andR_(d) are as defined above), a R_(e)R_(e)′N—CO—NR_(e)″—R_(d)-group(R_(e), R_(e)′ and R_(e)″ are the same or different, R_(e) and R_(e)′are as defined above, R_(e)″ has the same meaning as that of R_(e) andR_(d) is as defined above), aR_(e)R_(e)′N—C(═NR_(e)″)—NR_(e)′″—R_(d)-group (R_(e), R_(e)′, R_(e)″ andR_(e)′″ are the same or different, R_(e), R_(e)′ and R_(e)″ are asdefined above, R_(e)′″ has the same meaning as that of R_(e), and R_(d)is as defined above), a R_(b)—SO₂—NR_(e)—R_(d)-group (R_(b), R_(e) andR_(d) are as defined above), a R_(e)R_(e)′N—SO₂—R_(d)-group (R_(e),R_(e)′ and R_(d) are as defined above), a C2-C10 alkenyl group or aC2-C10 alkynyl group.];

-   (2) a Y₀ group:

a M_(b0)-R_(d)-group [M_(b0) represents a M_(c0) group {M_(c0)represents a M_(d0)-R_(d)′-group {M_(d0) represents a 6 to 10-memberedaryl group optionally substituted with a M_(a)-group (M_(a) is asdefined above), or a 5 to 10-membered heteroaryl group optionallysubstituted with a M_(a)-group (M_(a) is as defined above), a 3 to10-membered hydrocarbon ring or heterocycle optionally substituted witha M_(a)-group (M_(a) is as defined above) and optionally containing anunsaturated bond, or

a (b₀)-group (in (b₀), G₀ constitutes a saturated or unsaturatednon-aromatic 5 to 14-membered hydrocarbon ring or heterocycle optionallyhaving a substituent),

a (c₀)-group (in (c₀), J₀ may contain a nitrogen atom, and constitutesan aromatic 5 to 7-membered ring),

a (d₀)-group {d₀ constitutes a 5 to 12-membered hydrocarbon ringsubstituted with a carbonyl group or a thiocarbonyl group and, further,optionally substituted with an oxy group, a thio group, a —NR₁-group {R₁represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10 alkylgroup substituted with a halogen atom or a R₂—B₁-group (R₂ represents aC1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10 alkynyl group,and a B₁ represents an oxy group, a thio group, a sulfinyl group orsulfonyl group), or a C3-C10 alkenyl group, or a C3-C10 alkynyl group},a sulfinyl group or a sulfonyl group} or

an (e₀)-group {e₀ represents a 5 to 12-membered hydrocarbon ringoptionally substituted with a carbonyl group, a thiocarbonyl group, anoxy group, a thio group, a —NR₁-group (R₁ is as defined above), asulfinyl group or a sulfonyl group}, R_(d)′ is the same as or differentfrom R_(d), and has the same meaning as that of R_(d)}}, aM_(c0)-B_(a)-group (M_(c0) and B_(a) are as defined above), aM_(c0)-CO-group (M_(c0) is as defined above), a M_(c0)-CO—O-group(M_(c0) is as defined above), a M_(c0)O—CO-group (M_(c0) is as definedabove), a M_(c0)R_(e)N-group (M_(c0) and R_(e) are as defined above), aM_(c0)-CO—NR_(e)-group (M_(c0) and R_(e) are as defined above), aM_(c0)O—CO—NR_(e)-group (M_(c0) and R_(e) are as defined above), aM_(c0)R_(e)N—CO-group (M_(c0) and R_(e) are as defined above), aM_(c0)R_(e)N—CO—NR_(e)′-group (M_(c0), R_(e) and R_(e)′ are as definedabove), a M_(c0)R_(e)N—C(═NR_(e)′)—NR_(e)″-group (M_(c0), R_(e), R_(e)′and R_(e)″ are as defined above), a M_(c0)-SO₂—NR_(e)-group (M_(c0) andR_(e) are as defined above) or M_(c0)R_(e)N—SO₂-group (M_(c0) and R_(e)are as defined above), and R_(d) is as defined above.];

-   (3) a Z₀ group: a group which is a 5 to 12-membered hydrocarbon ring    or heterocycle ring optionally having a halogen atom, a C1-C10    alkoxy group, a C3-C10 alkenyloxy group, a C3-C10 alkynyloxy group,    a carbonyl group, a thiocarbonyl group, an oxy group, a thio group,    a sulfinyl group or a sulfonyl group, is an aromatic or non-aromatic    monocyclic or fused ring, and is fused with an A ring;-   III. Q_(A0) represents a hydroxyl group, a (b₀)-group ((b₀) is as    defined above), an A₉-B₆—B_(c)-group [A₉ represents a substituent of    the following A₇ group or A₈ group, B₆ represents a carbonyl group    or a thiocarbonyl group, and B_(c) represents an oxy group or a    —N((O)_(m)R₁)-group {m represents 0 or 1, and R₁ represents a    hydrogen atom, or a C1-C10 alkyl group, or a C2-C10 alkyl group    substituted with a halogen atom or a R₂—B₁-group (R₂ represents a    C1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10 alkynyl    group, and B₁ represents an oxy group, a thio group, a sulfinyl    group or a sulfonyl group), or a C3-C10 alkenyl group, or a C3-C10    alkynyl group}, provided that when A₉ is a hydrogen atom, then B_(c)    is not a sulfonyl group], an A₇″-SO₂—B_(c)-group (A₇″ represents a    substituent of the following A₇″ group, and B_(c) is as defined    above), an A₈-SO₂—B_(c)-group (A₈ represents a substituent of the    following A₈ group, and B_(c) is as defined above, provided that A₈    is not a hydrogen atom), a R₁R₁′N—SO₂—B_(c)-group (R₁ is as defined    above, R₁′ and R₁ are the same or different, and has the same    meaning as that of R₁, and B_(c) is as defined above), a    (b₀)—SO₂—B_(c)-group ((b₀) and B_(c) are as defined above), an    A₉′-B_(c)-group (A₉′ represents a substituent of the following A₇′    group or A₈′ group, and B_(c) is as defined above), a    D₅-R₄—B_(c)-group (D₅ represents a substituent of the following D₅    group, R₄ represents a C1-C10 alkylene group, and B_(c) is as    defined above), a M_(c0)-B₃—B_(c)-group (B₃ represents a carbonyl    group, a thiocarbonyl group or a sulfonyl group, and M_(c0) and    B_(c) are as defined above) or a M_(c0)-B_(c)-group (M_(c0) and    B_(c) are as defined above);-   (1) an A₇ group:

a C2-C10 alkenyl group optionally substituted with a halogen atom, aC2-C10 alkynyl group, a C3-C10 haloalkynyl group, a R₂—B₁—R₄-group (R₂and B₁ are as defined above, and R₄ is as defined above), a D₄-R₄-group(D₄ represents a substituent of the following D₄ group, and R₄ is asdefined above), a D₅-R₄-group (D₅ represents a substituent of thefollowing D₅ group, and R₄ is as defined above), a D₁-R₄-group {D₁represents a substituent of the following D₁-group, and R₄ is as definedabove}, a (b₀)-R₄-group ((b₀) is as defined above, and R₄ is as definedabove), a (c₀)-R₄-group ((c₀) is as defined above, and R₄ is as definedabove), a D₂-R₄-group {D₂ represents a substituent of the following D₂group, and R₄ is as defined above}, a D₃-R₄-group {D₃ represents asubstituent of the following D₃ group, and R₄ is as defined above}, anA₄-SO₂—R₄-group {A₄ represents a (b₀)-group ((b₀) is as defined above),a (c₀)-group ((c₀) is as defined above) or a R₁R₁′N-group (R₁ and R₁′are as defined above), and R₄ is as defined above} or an A₂-CO—R₄-group(A₂ represents a substituent of the following A₂ group, and R₄ is asdefined above);

-   (2) an A₈ group: a hydrogen atom, or a C1-C10 alkyl group optionally    substituted with a halogen atom;-   (3) an A₇′ group: a C3-C10 alkenyl group optionally substituted with    a halogen atom, a C3-C10 alkynyl group optionally substituted with a    halogen atom, a R₂—B₁—R₄′-group (R₂ and B₁ are as defined above, and    R₄′ represents a C2-C10 alkylene group), a D₄-R₄′-group (D₄ and R₄′    are as defined above), a D₁-R₄′-group (D₁ and R₄′ are as defined    above), a (b₀)-R₄′-group ((b₀) and R₄′ are as defined above), a    (c₀)-R₄′-group ((c₀) and R₄′ are as defined above), a D₂-R₄-group    (D₂ and R₄ are as defined above), a D₃-R₄′-group (D₃ and R₄′ are as    defined above) or an A₂-CO—R₄-group (A₂ and R₄ are as defined    above);-   (4) an A₈′ group: a C1-C10 alkyl group or C2-C10 haloalkyl group;-   (5) an A₇″ group: a C2-C10 alkenyl group, a C3-C10 alkenyl group    substituted with a halogen atom, a C3-C10 alkynyl group optionally    substituted with a halogen atom, a R₂—B₁—R₄′-group (R₂, B₁ and R₄′    are as defined above), a D₄-R₄′-group (D₄ and R₄′ are as defined    above), a D₅-R₄-group (D₅ and R₄ are as defined above), a    D₁-R₄′-group (D₁ and R₄′ are as defined above), (b₀)-R₄′-group ((b₀)    and R₄′ are as defined above), a (c₀)-R₄′-group ((c₀) and R₄′ are as    defined above), a D₂-R₄-group (D₂ and R₄ are as defined above), a    NO₂—R₄-group (R₄ is as defined above) or an A₂-CO—R₄-group (A₂ and    R₄ are as defined above);-   (i) a D₄-group: a hydroxy group or an A₁-O-group [A₁ represents a    R₃—(CHR₀)_(m)—(B₂—B₃)-_(m)′-group {R₃ represents a hydrogen atom, or    a C1-C10 alkyl group optionally substituted with a halogen atom or a    R₂—B₁-group (R₂ and B₁ are as defined above), or a C2-C10 alkenyl    group, or a C2-C10 alkynyl group, R₀ represents a hydrogen atom, a    C1-C10 alkyl group or a C2-C10 haloalkyl group, m is as defined    above, B₂ represents a single bond, an oxy group, a thio group or a    —N((O)_(n)R₁′)-group (R₁′ is as defined above, and n represents 0 or    1), B₃ is as defined above, m′ represents 0 or 1 and, when B₃ is a    sulfonyl group, then m is 0, and R₃ is not a hydrogen atom}];-   (ii) a D₅ group: an O═C(R₃)-group (R₃ is as defined above), an    A₁-(O)—N═C(R₃)-group (A₁, n and R₃ are as defined above), a    R₁—B₀—CO—R₄—(O)_(n)—N═C(R₃)-group [R₁, R₄, n and R₃ are as defined    above, and B₀ represents an oxy group, a thio group or a    —N((O)_(m)R₁′)-group (R₁′ and m are as defined above)], a    D₂-R₄—(O)_(n)—N═C(R₃)-group (D₂, R₄, n and R₃ are as defined above)    or a R₁A₁N—N═C(R₃)-group (R₁, A₁ and R₃ are as defined above);-   (iii) a D₁ group: a (R₁—(O)_(k)-)A₁N—(O)_(k)′-group (R₁ and A₁ are    as defined above, and k and k′ are the same or different and    represent 0 or 1);-   (iv) a D₂ group: a cyano group, a R₁R₁′NC(═N—(O)_(n)-A₁)-group (R₁,    R₁′, n and A₁ are as defined above), an A₁N═C(—OR₂)-group (A₁ and R₂    are as defined above) or a NH₂—CS-group;-   (v) a D₃ group: a nitro group or a R₁OSO₂-group (R₁ is as defined    above);-   (vi) an A₂ group:-   1) an A₃-B₄-group-   [A₃ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10    haloalkyl group, or a C2-C10 alkenyl group optionally substituted    with a halogen atom, or a C3-C10 alkynyl group optionally    substituted with a halogen atom, or a R_(a)—(R₄)_(m)-group (R_(a)    represents a phenyl group, a pyridyl group, a furyl group or a    thienyl group, optionally substituted with a halogen atom, C1-C10    alkyl group, a C1-C10 alkoxy group or a nitro group, R₄ and m are as    defined above), or a C1-C10 alkyl group substituted with a    (b₀)-R₄-group ((b₀) and R₄ are as defined above), a ((c₀)-R₄-group    ((c₀) and R₄ are as defined above), a R₂—B₁—R₄-group (R₂, B₁ and R₄    are as defined above), a D₄-R₄-group (D₄ and R₄ are as defined    above), a D₅-group (D₅ is as defined above), a D₁-R₄-group (D₁ and    R₄ are as defined above), a D₂-group (D₂ is as defined above), a    D₃-R₄-group (D₃ and R₄ are as defined above) or an R₄—SO₂—R₄-group    {A₄ is as defined above, and R₄ is as defined above};

B₄ represents an oxy group, a thio group or a —N((O)_(m)R₁) group (R₁and m are as defined above), provided that when B₄ is a thio group, thenA₃ is not a hydrogen atom.];

-   2) a R₁—B₄—CO—R₄—B₄′-group (R₁, B₄ and R₄ are as defined above, B₄′    is the same as or different from B₄, and has the same meaning as    that of B₄, provided that when B₄ is a thio group, then R₂ is not    hydrogen atom) or a D₂-R₄—B₄-group (D₂, R₄ and B₄ are as defined    above);-   3) a R₂—SO₂—NR₁-group (R₂ is as defined above, provided that a    hydrogen atom is excluded; R₁ is as defined above);-   4) a (b₀)-group ((b₀) is as defined above);-   5) a (c₀)-group ((c₀) is as defined above); or-   6) a R₁-A₁N—NR₁′-group (R₁, A₁ and R₁′ are as defined above);-   IV. W_(A0) represents an oxygen atom or a —NT_(A0)-group [T_(A0)    represents a hydrogen atom, an A₉′ group (A₉′ is as defined above),    a D₅-R₄-group (D₅ and R₄ are as defined above) or a M_(c0)-group    (M_(c0) is as defined above)];-   V. K_(A0) represents a hydrogen atom, a halogen atom or a C1-C10    alkyl group, L_(A0) represents a hydrogen atom, a C1-C10 alkyl group    or a M_(b0)-group (M_(b0) is as defined above), or K_(A0) and L_(A0)    may form a C1-C10 alkylene group, or a C1-C10 alkenylene group    optionally substituted with single or the same or different plural    M_(a) groups, provided that when an A ring is a benzene ring, W_(A0)    is an oxygen atom, L_(A0) is a methyl group, K_(A0) is a hydrogen    atom, and Q_(A0) is a C1-C4 alkoxy group, a C3-C4 alkenyloxy group    or a C3-C4 alkynyloxy group, then q is not 0 and, when an A ring is    a benzene ring, W_(A0) is an oxygen atom, L_(A0) is a methyl group,    K_(A0) is a hydrogen atom, and Q_(A0) is a C1-C4 alkoxy group, a    C3-C4 alkenyloxy group or a C3-C4 alkynyloxy group, then q is 1, and    Y_(A0) is not a halogen atom, or a C1-C4 alkyl group optionally    substituted with a halogen atom or a C1-C4 alkoxy group, or a nitro    group, or a C1-C4 alkoxy group, or a RB-group (R represents a C1-C4    haloalkyl group, and B represents an oxy group or a thio group) and,    when A is a benzene ring, W_(A0) is an oxygen atom, L_(A0) and    K_(A0) form a 1,3-butadienylene group, and Q_(A0) is a methoxy    group, q is 1, and Y_(A0) is not a methoxy group or an ethoxy group    and, when A is a benzene ring, W_(A0) is an oxygen atom, L_(A0) and    K_(A0) form a 1,3-butadienylene group, and Q_(A0) is a hydroxy    group, then q is 1, and Y_(A0) is not an ethoxy group; and the “as    defined above” in the same symbol between a plurality of    substituents indicates that the plurality of the substituents    independently represent the same meaning as that described above    and, between the plurality of substituents, a selection range of    selected substituents is the same, while the selected substituents    may be the same or the different as far as they are selected in the    range]; and an inert carrier;

3. A I type collagen gene transcription suppressing composition, whichcomprises a cinnamoyl compound represented by the formula (III):

[wherein

-   I. A represents a benzene ring or a pyridine ring;-   II. In (Y_(A))_(q), Y_(A) is a substituent on a carbon atom, and    represents a substituent of the following X group or Y group, q    represents 0, 1, 2, 3, 4 or 5, when q is 2 or more, Y_(A)'s are the    same or the different and, when q is 2 or more, the adjacent two    same or different Y_(A)'s constitute a group of a Z group, and may    be fused with an A ring;-   (1) a X group: a M_(a)-group [M_(a) represents a R_(b)-group (R_(b)    represents a C1-C10 alkyl group optionally substituted with a    halogen atom), a halogen atom, a nitro group, a cyano group, a    hydroxy group, a R_(c)—B_(a)—R_(d)-group (R_(c) represents a C1-C10    alkyl group optionally substituted with a halogen atom, B_(a)    represents an oxy group, a thio group, a sulfinyl group or a    sulfonyl group, and R_(d) represents a single bond or a C1-C10    alkylene group), a HOR_(d)-group (R_(d) is as defined above), a    R_(e)—CO—R_(d)-group (R_(e) represents a hydrogen atom, or a C1-C10    alkyl group optionally substituted with a halogen atom, and R_(d) is    as defined above), a R_(e)—CO—O—R_(d)-group (R_(e) and R_(d) are as    defined above), a R_(e)O—CO—R_(d)-group (R_(e) and R_(d) are as    defined above), a HO—CO—CH═CH-group, a R_(e)R_(e)′N—R_(d)— group    (R_(e) and R_(e)′ are the same or different, R_(e) is as defined    above, R_(e)′ has the same meaning as that of R_(e), and R_(d) is as    defined above), a R_(e)—CO—NR_(e)′—R_(d)-group (R_(e), R_(e)′—R_(d)    are as defined above), a R_(b)O—CO—N(R_(e))—R_(d)-group (R_(b),    R_(e) and R_(d) are as defined above), a R_(e)R_(e)′N—CO—R_(d)-group    (R_(e), R_(e)′ and R_(d) are as defined above), a    R_(e)R_(e)′N—CO—NR_(e)″—R_(d)-group (R_(e), R_(e)″ and R_(e)″ are    the same or different R_(e) and R_(e)′ are as defined above, R_(e)″    has the same meaning as that of R_(e), and R_(d) is as defined    above), a R_(e)R_(e)′N—C(═NR_(e)″)—NR_(e)′″—R_(d)-group (R_(e),    R_(e)′, R_(e)″ and R_(e)′″ are the same or different, R_(e), R_(e)′    and R_(e)″ are as defined above, R_(e)′″ has the same meaning as    that of R_(e) and R_(d) is as defined above), a    R_(b)—SO₂—NR_(e)—R_(d)-group (R_(b), R_(e) and R_(d) are as defined    above), R_(e)R_(e)′N—SO₂—R_(d)-group (R_(e), R_(e)″ and R_(d) are as    defined above), a C2-C10 alkenyl group or a C2-C10 alkynyl group];-   (2) a Y group: a M_(b)-R_(d)-group [M_(b) represents a M_(c)-group    {M_(c) represents a M_(d)-R_(d)′-group {M_(d) represents a phenyl    group optionally substituted with a M_(a)-group (M_(a) is as defined    above), or a pyridyl group optionally substituted with a M_(a)-group    (M_(a) is as defined above), or a naphthyl group optionally    substituted with a M_(a)-group (M_(a) is as defined above), or

a (b)-group {in (b), G₁, G₂, G₄ and G₅ represent a methylene group whichis connected to an adjacent atom with a single bond and may besubstituted with a methyl group, or a methine group which is connectedto an adjacent atom with a double bond, G₃ represents a single bond, ora double bond, or a C1-C10 alkylene group optionally substituted with amethyl group, an oxy group, a thio group, a sulfinyl group, a sulfonylgroup or a-NR₁-group {R₁ represents a hydrogen atom, or a C1-C10 alkylgroup, or a C2-C10 alkyl group substituted with a halogen atom or aR₂—B₁-group (R₂ represents a C1-C10 alkyl group, a C3-C10 alkenyl groupor a C3-C10 alkynyl group, and B₁ represents an oxy group, a thio group,a sulfinyl group or a sulfonyl group), or a C3-C10 alkenyl group, or aC3-C10 alkynyl group), or a C2-C10 alkenylene group optionallysubstituted with a methyl group, an oxy group, a thio group, a sulfinylgroup, a sulfonyl group or a —NR₁-group (R₁ is as defined above)},

a (c)-group (in (c), J₁, J₂ and J₃ are the same or different, andrepresent a methine group optionally substituted with a methine group,or a nitrogen atom),

a (d)-group (l is 2, 3 or 4, and B_(b) represents an oxy group or a thiogroup) or

an (e)-group (l and B_(b) are as defined above), R_(d)′ is the same asor different from R_(d), and has the same meaning as that of R_(d)}}, aM_(c)-B_(a)-group (M_(c) and B_(a) are as defined above), aM_(c)-CO-group (M_(c) is as defined above), a M_(c)-CO—O-group (M_(c) isas defined above), a M_(c)O—CO-group (M_(c) is as defined above), aM_(c)R_(e)N-group (M_(c) and R_(e) are as defined above), aM_(c)-CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)O—CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO—NR_(e)′-group (M_(c), R_(e) and R_(e)′ are as definedabove), a M_(c)R_(e)N—C(═NR_(e)′)—NR_(e)″-group (M_(c), R_(e), R_(e)′and R_(e)″ are as defined above), a M_(c)-SO₂—NR_(e)-group (M_(c) andR_(e) are as defined above) or a M_(c)R_(e)N—SO₂-group (M_(c) and R_(e)are as defined above), and R_(d) is as defined above];

-   (3) a Z group: a —N═C(Y_(a))—Y_(a)′-group (Y_(a) represents a    hydrogen atom, or a C1-C10 alkyl group optionally substituted with a    halogen atom, or a C1-C10 alkoxy group, Y_(a)′ represents an oxy    group, or a thio group, or an imino group optionally substituted    with a C1-C10 alkyl group), a —Y_(b)—Y_(b)′—Y_(b)″-group (Y_(b) and    Y_(b)″ are the same or different, and represent a methylene group,    or an oxy group, or a thio group, or a sulfinyl group, or an imino    group optionally substituted with a C1-C10 alkyl group, and Y_(b)′    represents a C1-C4 alkylene group optionally substituted with a    halogen atom, or a C1-C4 alkylene group optionally having an oxo    group) or a —Y_(c)—O—Y_(c)′—O-group (Y_(c) and Y_(c)′ are the same    or different, and represent a C1-C10 alkylene group);-   III. Q_(A) represents a hydroxyl group, a (b)-group ((b) is as    defined above), an A₉-B₆—B_(c)-group (A₉ represents a substituent of    the following A₇ group or A₈ group, B₆ represents a carbonyl group    or a thiocarbonyl group, B_(c) represents an oxy group or a    —N((O)_(m)R₁)-group (m represents 0 or 1, and R₁ is as defined    above), provided that when A₉ is a hydrogen atom, B_(c) is not a    sulfonyl group], an A₇″-SO₂—B_(c)-group (A₇″ represents a    substituent of the following A₇″ group, and B_(c) is as defined    above), an A₈-SO₂—B_(c)-group (A₈ represents a substituent of the    following A₈ group, B_(c) is as defined above, provided that A₈ is    not a hydrogen atom), a R₁R₁′N—SO₂—B_(c)-group (R₁ is as defined    above, R₁′ is the same as or different from R₁, and has the same    meaning as that of R₁, and B_(c) is as defined above), a    (b)-SO₂—B_(c)-group ((b) and B_(c) are as defined above), an    A₉′-B_(c)-group (A₉′ represents a substituent of the following A₇′    group or A₈′ group, and B_(c) is as defined above), a    D₅-R₄—B_(c)-group (D₅ represents a substituent of the following D₅    group, R₄ represents a C1-C10 alkylene group, and B_(c) is as    defined above), a M_(c)-B₃—B_(c)-group (B₃ represents a carbonyl    group, a thiocarbonyl group or a sulfonyl group, and M_(c) and B_(c)    are as defined above) or a M_(c)-B_(c)-group (M_(c) and B_(c) are as    defined above);-   (1) an A₇ group:

a C2-C10 alkenyl group optionally substituted with a halogen atom, aC2-C10 alkynyl group, a C3-C10 haloalkynyl group, a R₂—B₁—R₄-group (R₂and B₁ are as defined above, and R₄ is as defined above), a D₄-R₄-group(D₄ represents a substituent of the following D₄ group, and R₄ is asdefined above), a D₅-R₄-group (D₅ represents a substituent of thefollowing D₅ group, and R₄ is as defined above), a D₁-R₄-group {D₁represents a substituent of the following D₁ group, and R₄ is as definedabove}, a (b)-R₄-group ((b) is as defined above, and R₄ is as definedabove), a (c)-R₄-group ((c) is as defined above, and R₄ is as definedabove), a D₂-R₄-group {D₂ represents a substituent of the following D₂group, and R₄ is as defined above}, a D₃-R₄-group {D₃ represents asubstituent of the following D₃ group, and R₄ is as defined above}, anA₄-SO₂—R₄-group {A₄ represents a (b)-group ((b) is as defined above), a(c)-group ((c) is as defined above) or a R₁R₁′N-group (R₁ and R₁′ are asdefined above), and R₄ is as defined above} or an A₂-CO—R₄-group (A₂represents a substituent of the following A₂ group, and R₄ is as definedabove);

-   (2) an A₈ group: a hydrogen atom, or a C1-C10 alkyl group optionally    substituted with a halogen atom;-   (3) an A₇′ group: a C3-C10 alkenyl group optionally substituted with    a halogen atom, a C3-C10 alkynyl group optionally substituted with a    halogen atom, a R₂—B₁—R₄′-group (R₂ and B₁ are as defined above, and    R₄′ represents a C2-C10 alkylene group), a D₄-R₄′-group (D₄ and R₄′    are as defined above), a D₁-R₄′-group (D₁ and R₄′ are as defined    above), a (b)-R₄′-group ((b) and R₄′ are as defined above), a    (c)-R₄′-group ((c) and R₄′ are as defined above), a D₂-R₄-group (D₂    and R₄ are as defined above), a D₃-R₄′-group (D₃ and R₄′ are as    defined above) or an A₂-CO—R₄-group (A₂ and R₄ are as defined    above);-   (4) an A₈′ group: a C1-C10 alkyl group or a C2-C10haloalkyl group;-   (5) an A₇″ group: a C2-C10 alkenyl group, a C3-C10 alkenyl group    substituted with a halogen atom, a C3-C10 alkynyl group optionally    substituted with a halogen atom, a R₂—B₁—R₄′-group (R₂, B₁ and R₄′    are as defined above), a D₄-R₄′-group (D₄ and R₄′ are as defined    above), a D₅-R₄-group (D₅ and R₄ are as defined above), a    D₁-R₄′-group (D₁ and R₄′ are as defined above), a (b)-R₄′-group ((b)    and R₄′ are as defined above), a (c)-R₄′-group ((c) and R₄′ are as    defined above), a D₂-R₄-group (D₂ and R₄ are as defined above), a    NO₂—R₄-group (R₄ is as defined above) or an A₂-CO—R₄-group (A₂ and    R₄ are as defined above);-   (i) a D₄ group: a hydroxyl group or an A₁-O-group [A₁ represents a    R₃—(CHR₀)_(m)—(B₂—B₃)_(m′)-group {R₃ represents a hydrogen atom, or    a C1-C10 alkyl group optionally substituted with a halogen atom or a    R₂—B₁-group (R₂ and B₁ are as defined above), or a C2-C10 alkenyl    group, or a C2-C10 alkynyl group, R₀ represents a hydrogen atom, a    C1-C10 alkyl group or a C2-C10haloalkyl group, m is as defined    above, B₂ represents a single bond, an oxy group, a thio group or a    —N(O)_(n)R₁′-group (R₁′ is as defined above, and n represents 0 or    1), B₃ is as defined above, m′ represents 0 or 1 and, when B₃ is a    sulfonyl group, m is 0, and R₃ is not a hydrogen atom}];-   (ii) a D₅ group: O═C(R₃)-group (R₃ is as defined above), an    A₁-(O)_(n)—N═C(R₃)-group (A₁, n and R₃ are as defined above), a    R₁—B₀—CO—R₄—(O)_(n)—N═C(R₃)-group [R₁, R₄, n and R₃ are as defined    above, and B₀ represents an oxy group, a thio group or a    —N(O)_(m)R₁′)-group (R₁′ and m are as defined above)], a    D₂-R₄—(O)_(n)—N═C(R₃)-group (D₂, R₄, n and R₃ are as defined above)    or a R₁A₁N—N═C(R₃)-group (R₁, A₁ and R₃ are as defined above);-   (iii) a D₁ group: a (R₁—(O)_(k)-)A₁N—(O)_(k′)-group (R₁ and A₁ are    as defined above, and k and k′ are the same or different, and    represent 0 or 1);-   (iv) a D group: a cyano group, a R₁R₁′NC′(═N—(O)_(n)-A₁)-group (R₁,    R₁′, n and A₁ are as defined above), an A₁N═C(—O—) group (A₁ and R₂    are as defined above) or a NH₂—CS-group;-   (v) a D₃ group: a nitro group or a R₁OSO₂-group (R₁ is as defined    above);-   (vi) an A₂ group:-   1) an A₃-B₄-group-   [A₃ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10    haloalkyl group, or a C2-C10 alkenyl group optionally substituted    with a halogen atom, or a C3-C10 alkynyl group optionally    substituted with a halogen atom, or a R_(a)—(R₄)_(m)-group (R_(a)    represents a phenyl group, a pyridyl group, a furyl group or a    thienyl group, optionally substituted with a halogen atom, a C1-C10    alkyl group, a C1-C10 alkoxy group or a nitro group, and R₄ and m    are as defined above), or a C1-C10 alkyl group substituted with a    (b)-R₄-group ((b) and R₄ are as defined above), a (c)-R₄-group ((c)    and R₄ are as defined above), a R₂—B₁—R₄-group (R₂, B₁ and R₄ are as    defined above), a D₄-R₄-group (D₄ and R₄ are as defined above), a    D₅-group (D₅ is as defined above), a D₁-R₄-group (D₁ and R₄ are as    defined above), a D₂-group (D₂ is as defined above), a D₃-R₄-group    (D₃ and R₄ are as defined above) or an A₄-SO₂—R₄-group {A₄ is as    defined above, and R₄ is as defined above};

B₄ represents an oxy group, a thio group or a —N((O)_(m)R₁)— group (R₁and m are as defined above) provided that when B₄ is a thio group, A₃ isnot a hydrogen atom];

-   2) a R₁—B₄—CO—R₄—B₄′-group (R₁, B₄ and R₄ are as defined above, B₄′    is the same as or different from B₄, and has the same meaning as    that of B₄, provided that when B₄ is a thio group, a R₂ is not a    hydrogen atom) or a D₂-R₄—B₄-group (D₂, R₄ and B₄ are as defined    above);-   3) a R₂—SO₂—NR₁-group (R₂ is as defined above, provided that a    hydrogen atom is excluded, and R₁ is as defined above);-   4) a (b)-group ((b) is as defined above);-   5) a (c)-group ((c) is as defined above); or-   6) a R₁A₁N—NR₁′-group (R₁, A₁ and R₁′ are as defined above);-   IV. W_(A) represents an oxygen atom or a —NT_(A)-group [T_(A)    represents a hydrogen atom, an A₉′-group (A₉′ is as defined above),    a D₅-R₄-group (D₅ and R₄ are as define above) or a M_(c)-group    (M_(c) is as defined above)];-   V. K_(A) represents a hydrogen atom, a halogen atom or a C1-C10    alkyl group, L_(A) represents a hydrogen atom, a C1-C10 alkyl group    or a M_(b)-group (M_(b) is as defined above), or K_(A) and L_(A) may    form a C1-C10 alkylene group or a    —C(M_(a)′)=C(M_(a)″)-C(M_(a)′″)=C(M_(a)″″)-group (M_(a)′, M_(a)″,    M_(a)′″ and M_(a)″″ are the same or different, are the same as or    different from M_(a), and represent a hydrogen atom or M_(a)); and

provided that when an A ring is a benzene ring, W_(A) is an oxygen atom,L_(A) is a methyl group, K_(A) is a hydrogen atom, and Q_(A) is a C1-C10alkoxy group, a C3-10 alkenyloxy group or a C3-C10 alkynyloxy group,then q is not 0 and, when an A ring is a benzyl ring, W_(A) is an oxygenatom, L_(A) is a methyl group, K_(A) is a hydrogen atom, and Q_(A) is aC1-C10 alkoxy group, a C3-C10 alkenyloxy group or a C3-C10 alkynyloxygroup, then q is 1, and Y_(A) is not a halogen atom, or C1-C10 alkylgroup optionally substituted with a halogen atom or a C1-C10 alkoxygroup, or a nitro group, or a C1-C10 alkoxy group, or a RB-group (Rrepresents a C1-C10haloalkyl group and B represents an oxy group or athio group) and, when A is a benzene ring, W_(A) is an oxygen atom,L_(A) and K_(A) form a 1,3-butadienylene group, and Q_(A) is a hydroxylgroup or a C1-C10 alkoxy group, then q is 1, and Y_(A) is not a C1-C10alkoxy group; and

the “as defined above” in the same symbol between a plurality ofsubstituents indicates that the plurality of substituents independentlyrepresent the same meaning as that described above and, between theplurality of substituents, a selection range of selected substituents isthe same, while the selected substituents may be the same or differentas far as they are selected in the range]; and an inert carrier;

4. A I type collagen gene transcription suppressing composition, whichcomprises a 2H-pyran-2-one compound represented by the formula (IV):

[wherein

-   I. A represents a benzene ring or a pyridine ring;-   II. In (X_(a))_(p), X_(a) is a substituent on a carbon atom, and    represents a halogen atom, or a C1-C10 alkyl group optionally    substituted with a halogen atom or a C1-C10 alkoxy group, or a nitro    group, a C1-C10 alkoxy group, or a RB-group (R represents a C1-C10    haloalkyl group, and B represents an oxy group or a thio group), p    represents 0, 1, 2, 3 or 4 and, when p is 2 or more, X_(a)'s are the    same or different;-   III. In (Y_(a))_(q), Y_(a) is a substituent on a carbon atom, and    represents a substituent of the following X₁ group or Y₁ group, q    represents 0, 1, 2, 3, 4 or 5, when q is 2 or more, Y_(a)'s are the    same or different and, when q is 2 or more, the adjacent two same or    different Y_(a)'s constitute a Z₁ group, and may be fused with an A    ring;-   (1) a X₁ group:

a M_(a)-group [M_(a) represents a R_(b)-group (R_(b) represents a C1-C10alkyl group optionally substituted with a halogen atom), a halogen atom,a nitro group, a cyano group, a hydroxyl group, aR_(c)—B_(a)—R_(d)-group (R_(c) represents a C1-C10 alkyl groupoptionally substituted with a halogen atom, B_(a) represents an oxygroup, a thio group, a sulfinyl group or a sulfonyl group, and R_(d)represents a single bond or a C1-C10 alkylene group), a HOR_(d)-group(R_(d) is as defined above), a R_(e)—CO—R_(d)-group (R_(e) represents ahydrogen atom, or a C1-C10 alkyl group optionally substituted with ahalogen atom, and R_(d) is as defined above), a R_(e)—CO—O—R_(d)-group(R_(e) and R_(d) are as defined above), a R_(e)O—CO—R_(d)-group (R_(e)and R_(d) are as defined above), a HO—CO—CH═CH-group, aR_(e)R_(e)′N—R_(d)-group (R_(e) and R_(e)′ are the same or different,R_(e) is as defined above, R_(e)′ has the same meaning as that of R_(e),and R_(d) is as defined above), a R_(e)—CO—NR_(e)′—R_(d)-group (R_(e),R_(e)′ and R_(d) are as defined above), a R_(b)O—CO—N(R_(e))—R_(d)-group(R_(b), R_(e) and R_(d) are as defined above), aR_(e)R_(e)′N—CO—R_(d)-group (R_(e), R_(e)′ and R_(d) are as definedabove), a R_(e)R_(e)′N—CO—NR_(e)″—R_(d)-group (R_(e), R_(e)′ and R_(e)″are the same or different, R_(e) and R_(e)′ are as defined above, R_(e)″has the same meaning as that of R_(e), and R_(d) is as defined above), aR_(e)R_(e)′N—C(═NR_(e)″)—NR_(e)′″—R_(d)-group (R_(e), R_(e)′, R_(e)″ andR_(e)′″ are the same or different, R_(e), R_(e)′ and R_(e)″ are asdefined above, R_(e)′″ has the same meaning as that of R_(e), and R_(d)is as defined above), a R_(b)—SO₂—NR_(e)—R_(d)-group (R_(b), R_(e) andR_(d) are as defined above), a R_(e)R_(e)′N—SO₂—R_(d)-group (R_(e),R_(e)″ and R_(d) are as defined above), a C2-C10 alkenyl group or aC2-C10 alkynyl group], provided that when A represents a benzene ring, aX_(a)-group (X_(a) is as defined above) is excluded;

-   (2) a Y₁ group:

a M_(b)-R_(d)-group [M_(b) represents a M_(c)-group {M_(c) represents aM_(d)-R_(d)′-group {M_(d) represents a phenyl group optionallysubstituted with a M_(a)-group (M_(a) is as defined above), or a pyridylgroup optionally substituted with a M_(a)-group (M_(a) is as definedabove) or a naphthyl group optionally substituted with a M_(a)-group(M_(a) is as defined above), or

a (b)-group {in (b), G₁, G₂, G₄ and G₅ represent a methylene group whichis connected to an adjacent atom with a single bond and may besubstituted with a methyl group, or a methine group which is connectedto an adjacent atom with a double bond and may be substituted with amethyl group, and G₃ represents a single bond, or a double bond, or aC1-C10 alkylene group optionally substituted with a methyl group, an oxygroup, a thio group, a sulfinyl group, a sulfonyl group or a —NR₁-group{R₁ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10alkyl group substituted with a halogen atom or a R₂—B₁-group (R₂represents a C1-C10 alkyl group, a C—C10 alkenyl group or a C3-C10alkynyl group, and B₁ represents an oxy group, a thio group, a sulfinylgroup or a sulfonyl group), or a C3-C10 alkenyl group, or a C3-C10alkynyl group}, or a C2-C10 alkenylene group optionally substituted witha methyl group, an oxy group, a thio group, a sulfinyl group, a sulfonylgroup or a —NR₁-group (R₁ is as defined above)},

a (c)-group (in (c), J₁, J₂ and J₃ are the same or different, andrepresent a methine group optionally substituted with a methyl group, ora nitrogen atom),

a (d)-group (l is 2, 3 or 4, and B_(b) represents an oxy group, or athio group), or

an (e)-group (l and B_(b) are as defined above), R_(d)′ is the same asor different from R_(d), and has the same meaning as that of R_(d)}}, aM_(c)-B_(a)-group (M_(c) and B_(a) are as defined above), aM_(c)-CO-group (M_(c) is as defined above), a M_(c)-CO—O-group (M_(c) isas defined above), a M_(c)O—CO-group (M_(c) is as defined above), aM_(c)R_(e)N-group (M_(c) and R_(e) are as defined above), aM_(c)-CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)O—CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO—NR_(e)′-group (M_(c), R_(e) and R_(e)′ are as definedabove), a M_(c)R_(e)N—C(═NR_(e)′)—NR_(e)″-group (M_(c), R_(e), R_(e)′and R_(e)″ are as defined above), a M_(c)-SO₂—NR_(e)-group (M_(c) andR_(e) are as defined above) or a M_(c)R_(e)N—SO₂-group (M_(c) and R_(e)are as defined above), and R_(d) is as defined above];

-   (3) a Z₁ group:

a —N═C(Y_(a))—Y_(a)′-group (Y_(a) represents a hydrogen atom, or aC1-C10 alkyl group optionally substituted with a halogen atom, or aC1-C10 alkoxy group, and Y_(a)′ represents an oxy group, or a thiogroup, or an imino group optionally substituted with a C1-C10 alkylgroup), a —Y_(b)—Y_(b)′—Y_(b)″-group (Y_(b) and Y_(b)″ are the same ordifferent, and represent a methylene group, or an oxy group, or a thiogroup, or a sulfinyl group, or an imino group optionally substitutedwith a C1-C10 alkyl group, and Y_(b)′ represents a C1-C4alkylene groupoptionally substituted with a halogen atom, or a C1-C4 alkylene groupoptionally having an oxo group) or a —Y_(c)—O—Y_(c)′—O-group (Y_(c) andY_(c)′ are the same or different, and represent a C1-C10 alkylenegroup);

-   IV. Q_(A) represents a hydroxyl group, a (b)-group ((b) is as    defined above), an A₉-B₆—B_(c)-group [A₉ represents a substituent of    the following A₇ group or A₈ group, B₆ represents a carbonyl group    or a thiocarbonyl group, B_(c) represents an oxy group or a    —N((O)_(m)R₁)-group (m represents 0 or 1, and R₁ is as defined    above), provided that when A₉ is a hydrogen atom, B_(c) is not a    sulfonyl group], an A₇″-SO₂—B_(c)-group (A₇″ represents a    substituent of the following A₇″ group, and B_(c) is as defined    above), an A₈-SO₂—B_(c)-group (A₈ represents a substituent of the    following A₈ group, and B_(c) is as defined above, provided that A₈    is not a hydrogen atom), a R₁R₁′N—SO₂—B_(c)-group (R₁ is as defined    above, R₁′ is the same as or different from R₁, and has the same    meaning as that of R₁, and B_(c) is as defined above), a    (b)-SO₂—B_(c)-group ((b) and B_(c) are as defined above), an    A₉′-B_(c)-group (A₉′ represents a substituent of the following A₇′    group or A₈′ group, and B_(c) is as defined above), a    D₅-R₄—B_(c)-group (D₅ represents a substituent of the following D₅    group, R₄ represents a C1-C10 alkylene group, and B_(c) is as    defined above), M_(c)-B₃—B_(c)-group (B₃ represents a carbonyl    group, a thiocarbonyl group or a sulfonyl group and M_(c) and B_(c)    are as defined above) or a M_(c)-B_(c)-group (M_(c) and B_(c) are as    defined above);-   (1) an A₇ group:

a C2-C10 alkenyl group optionally substituted with a halogen atom, aC2-C10 alkynyl group, a C3-C10 haloalkynyl group, a R₂—B₁—R₄-group (R₂and B₁ are as defined above, and R₄ is as defined above), a D₄-R₄-group(D₄ represents a substituent of the following D₄ group, and R₄ is asdefined above), a D₅-R₄-group (D₅ represents a substituent of thefollowing D₅ group, R₄ is as defined above), a D₁-R₄-group {D₁represents a substituent of the following D₁ group, and R₄ is as definedabove}, a (b)-R₄-group {(b) is as defined above, and R₄ is as definedabove}, a (c)-R₄-group ((c) is as defined above, and R₄ is as definedabove), a D₂-R₄-group {D₂ represents a substituent of the following D₂group, and R₄ is as defined above}, a D₃-R₄-group {D₃ represents asubstituent of the following D₃ group, and R₄ is as defined above}, anA₄-SO₂—R₄-group {A₄ represents a (b)-group ((b) is as defined above), a(c)-group ((c) is as defined above) or a R₁R₁′N-group (R₁ and R₁′ are asdefined above), and R₄ is as defined above} or an A₂-CO—R₄-group (A₂represents a substituent of the following A₂ group, and R₄ is as definedabove);

-   (2) an A₈ group: a hydrogen atom, or a C1-C10 alkyl group optionally    substituted with a halogen atom;-   (3) an A₇′ group: a C3-C10 alkenyl group optionally substituted with    a halogen atom, a C3-C10 alkynyl group optionally substituted with a    halogen atom, a R₂—B₁—R₄′-group (R₂ and B₁ are as defined above, and    R₄′ represents a C2-C10 alkylene group), a D₄-R₄′-group (D₄ and R₄′    are as defined above), a D₁-R₄′-group (D₁ and R₄′ are as defined    above), a (b)-R₄′-group ((b) and R₄′ are as defined above), a    (c)-R₄′-group ((c) and R₄′ are as defined above), a D₂-R₄-group (D₂    and R₄ are as defined above), a D₃-R₄′-group (D₃ and R₄′ are as    defined above) or an A₂-CO—R₄-group (A₂ and R₄ are as defined    above);-   (4) an A₈′ group: a C1-C10 alkyl group or a C2-C10 haloalkyl group;-   (5) an A₇″ group: a C2-C10 alkenyl group, a C3-C10 alkenyl group    substituted with a halogen atom, a C3-C10 alkynyl group optionally    substituted with a halogen atom, a R₂—B₁—R₄′-group (R₂, B₁ and R₄′    are as defined above), a D₄-R₄′-group (D₄ and R₄′ are as defined    above), a D₅-R₄-group (D₅ and R₄ are as defined above), a    D₁-R₄′-group (D₁ and R₄′ are as defined above), (b)-R₄′-group ((b)    and R₄′ are as defined above), a (c)-R₄′-group ((c) and R₄′ are as    defined above), a D₂-R₄-group (D₂ and R₄ are as defined above), a    NO₂—R₄-group (R₄ is as defined above) or an A₂-CO—R₄-group (A₂ and    R₄ are as defined above);-   (i) a D₄ group: a hydroxyl group or an A₁-O-group [A₁ represents a    R₃—(CHR₀)_(m)—(B₂—B₃)_(m′)-group {R₃ represents a hydrogen atom, or    a C1-C10 alkyl group optionally substituted with a halogen atom or a    R₂—B₁-group (R₂ and B₁ are as defined above), or a C2-C10 alkenyl    group, or a C2-C10 alkynyl group, R₀ represents a hydrogen atom, a    C1-C10 alkyl group or a C2-C10 haloalkyl group, m is as defined    above, B₂ represents a single bond, an oxy group, a thio group or a    —N(O)_(n)R₁′)-group (R₁′ is as defined above, and n represents 0 or    1, B₃ is as defined above, m′ represents 0 or 1 and, when B₃ is a    sulfonyl group, m is 0, and R₃ is not a hydrogen atom)}];-   (ii) a D₅ group: an O═C(R₃)-group (R₃ is as defined above), an    A₁-(O)_(n)—N═C(R₃)-group (A₁, n and R₃ are as defined above), a    R₁—B₀—CO—R₄—(O)_(n)—N═C(R₃)-group [R₁, R₄, n and R₃ are as defined    above, and B₀ represents an oxy group, a thio group or a    —N((O)_(m)R₁′)-group (R₁′ and m are as defined above)], a    D₂-R₄—(O)_(n)—N═C(R₃-group (D₂, R₄, n and R₃ are as defined above)    or a R₁A₁N—N═C(R₃)-group (R₁, A₁ and R₃ are as defined above);-   (iii) a D₁ group: a (R₁—(O)_(k)-)A₁N—(O)_(k′)-group (R₁ and A₁ are    as defined above, and k and k′ are the same or different, and    represent 0 or 1);-   (iv) a D₂ group: a cyano group, a R₁R₁′NC(═N—(O)_(n)-A)-group (R₁,    R₁′, n and N₁ are as defined above), an A₁N═C(—OR₂)-group (A₁ and R₂    are as defined above) or a NH₂—CS-group.-   (v) a D₃ group: a nitro group or a R₁OSO₂-group (R₁ is as defined    above);-   (vi) an A₂ group:-   1) an A₃-B₄-group-   [A₃ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10    haloalkyl group, or a C2-C10 alkenyl group optionally substituted    with a halogen atom, or a C3-C10 alkynyl group optionally    substituted with a halogen atom, or a R_(a)—(R₄)_(m)-group (R_(a)    represents a phenyl group, a pyridyl group, a furyl group or a    thienyl group, optionally substituted with a halogen atom, a C1-C10    alkyl group, a C1-C10 alkoxy group or a nitro group, and R₄ and m    are as defined above), or a C1-C10 alkyl group substituted with a    (b)-R₄-group ((b) and R₄ are as defined above), a (c)-R₄-group ((c)    and R₄ are as defined above), a R₂—B₁—R₄-group (R₂, B₁ and R₄ are as    defined above), a D₄-R₄-group (D₄ and R₄ are as defined above), a    D₅-group (D₅ is as defined above), a D₁-R₄-group (D₁ and R₄ are as    defined above), a D₂-group (D₂ is as defined above), a D₃-R₄-group    (D₃ and R₄ are as defined above) or an A₄-SO₂—R₄-group {A₄ is as    defined above, and R₄ is as defined above}; B₄ represents an oxy    group, a thio group or a —N((O)_(m)R₁)-group (R₁ and m are as    defined above), provided that when B₄ is a thio group, A₃ is not a    hydrogen atom];-   2) a R₁—B₄—CO—R₄—B₄′-group (R₁, B₄ and R₄ are as defined above, B₄′    is the same as or different from B₄, and has the same meaning as    that of B₄, provided that when B₄ is a thio group, R₂ is not a    hydrogen atom) or a D₂-R₄—B₄-group (D₂, R₄ and B₄ are as defined    above);-   3) a R₂—SO₂—NR₁-group (R₂ is as defined above, provided that a    hydrogen atom is excluded, and R₁ is as defined above),-   4) a (b)-group ((b) is as defined above);-   5) a (c)-group ((c) is as defined above); or-   6) a R₁A₁N—NR₁′-group (R₁, R₁ and R₁′ are as defined above);-   V. K_(a) represents a hydrogen atom, a halogen atom or a C1-C10    alkyl group, L_(a) represents a hydrogen atom, a C1-C10 alkyl group    or a M_(b)-group (M_(b) is as defined above), or K_(a) and L_(a) may    form a C1-C10 alkylene group, provided that when K_(a) is a hydrogen    atom, L_(a) is a methyl group and an A ring is a benzene ring, p is    2, 3 or 4 in the case that q is 0; and

the “as defined above” in the same symbol between a plurality ofsubstituents indicates that the plurality of substituents independentlyrepresent the same meaning as that described above and, between theplurality of substituents, a selection range of selected substituents isthe same, while the selected substituents may be the same or differentas far as they are selected in a range]; and an inert carrier;

5. A 2H-pyran-2-one compound represented by the formula (V):

[wherein

-   I. A represents a benzene ring or a pyridine ring;-   II. In (X_(b))_(p), X_(b) is a substituent on a carbon atom, and    represents a halogen atom, or a C1-C10 alkyl group optionally    substituted with a halogen atom or a C1-C10 alkoxy group, or a nitro    group, or a C2-C10 alkoxy group, or a RB-group (R represents a    C1-C10 haloalkyl group, and B represents an oxy group or a thio    group), p represents 0, 1, 2, 3 or 4 and, when p is 2 or more,    X_(b)'s are the same or different;-   III. In (Y_(b))_(q), Y_(b) is a substituent on a carbon atom, and    represents a substituent of the following X₂ group or Y₂ group, q    represents 0, 1, 2, 3, 4 or 5, when q is 2 or more, Y_(b)'s are the    same or different and, when q is 2 or more, the adjacent two same or    different Y_(b)'s constitutes a group of a Z₂ group, and may be    fused with an A ring;-   (1) a X₂ group:

a M_(a)-group [M_(a) represents a R_(b)-group (R_(b) represents a C1-C10alkyl group optionally substituted with a halogen atom), a halogen atom,a nitro group, a cyano group, a hydroxy group, a R_(c)—B_(a)—R_(d)-group(R_(c) represents a C1-C10 alkyl group optionally substituted with ahalogen atom, B_(a) represents an oxy group, a thio group, a sulfinylgroup or a sulfonyl group, and R_(d) represents a single bond or aC1-C10 alkylene group), a HOR_(d)-group (R_(d) is as defined above), aR_(e)—CO—R_(d)-group (R_(e) represents a hydrogen atom, or a C1-C10alkyl group optionally substituted with a halogen atom, and R_(d) is asdefined above), a R_(e)—CO—O—R_(d)-group (R_(e) and R_(d) are as definedabove), a R_(e)O—CO—R_(d)-group (R_(e) and R_(d) are as defined above),a HO—CO—CH═CH-group, a R_(e)R_(e)′N—R_(d)-group (R_(e) and R_(e)′ arethe same or different, R_(e) is as defined above, R_(e)′ has the samemeaning as that of R_(e), and R_(d) is as defined above), aR_(e)—CO—NR_(e)′—R_(d)-group (R_(e), R_(e)′ and R_(d) are as definedabove), a R_(b)O—CO—N(R_(e))—R_(d)-group (R_(b), R_(e) and R_(d) are asdefined above), a R_(e)R_(e)′N—CO—R_(d)-group (R_(e), R_(e)′ and R_(d)are as defined above), a R_(e)R_(e)′N—CO—NR_(d)″—R_(d)-group (R_(e),R_(e)′ and R_(e)″ are the same or different, R_(e) has the same meaningas that of R_(e)′, R_(e)″ has the same meaning as that of R_(e), andR_(d) is as defined above), aR_(e)R_(e′)N—C(═NR_(e)″)—NR_(e)′″—R_(d)-group (R_(e), R_(e)′, R_(e)″ andR_(e)′″ are the same or different, R_(e), R_(e)′ and R_(e)″ are asdefined above, R_(e)′″ has the same meaning as that of R_(e), and R_(d)is as defined above), a R_(b)—SO₂—NR_(e)—R_(d)-group (R_(b), R_(e) andR_(d) are as defined above), a R_(e)R_(e)′N—SO₂—R_(d)-group (R_(e),R_(e)′ and R_(d) are as defined above), a C2-C10 alkenyl group or aC2-C10 alkynyl group], provided that, when A represents a benzene ring,then, a halogen atom, or a C1-C10 alkyl group optionally substitutedwith a halogen atom or a C1-C10 alkoxy group, or a nitro group, or aC1-C10 alkoxy group, or a RB-group (R and B are as described above) isexcluded;

-   (2) a Y₂ group:

a M_(b)-R_(d)-group [M_(b) represents a M_(c)-group {M_(c) represents aM_(d)-R_(d)′-group {M_(d) represents a phenyl group optionallysubstituted with a M_(a)-group (M_(a) is as defined above), or a pyridylgroup optionally substituted with a M_(a)-group (M_(a) is as definedabove), or a naphthyl group optionally substituted with a M_(a)-group(M_(a) is as defined above) or

a (b)-group {in (b), G₁, G₂, G₄ and G₅ represent a methylene group whichis connected to an adjacent atom with a single bond and may besubstituted with a methyl group, or a methine group which is connectedto an adjacent atom with a double bond and may be substituted with amethyl group, and G₃ represents a single bond, or a double bond, or aC1-C10 alkylene group optionally substituted with a methyl group, an oxygroup, a thio group, a sulfinyl group, a sulfonyl group, or a —NR₁-group{R₁ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10alkyl group substituted with a halogen atom or a R₂—B₁-group (R₂represents a C1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10alkynyl group, and B₁ represents an oxy group, a thio group, a sulfinylgroup or a sulfonyl group), or a C3-C10 alkenyl group, or a C3-C10alkynyl group}, or a C2-C10 alkenylene group optionally substituted witha methyl group, an oxy group, a thio group, a sulfinyl group, a sulfonylgroup or a NR₁— group (R₁ is as defined above)},

a (c)-group (in (c), J₁, J₂ and J₃ are the same or different, andrepresent a methine group optionally substituted with a methyl group, ora nitrogen atom),

a (d) group (l is 2, 3 or 4, and B_(b) represents an oxy group or a thiogroup) or

an (e)-group (l and B_(b) are as defined above), R_(d)′ is the same asor different from R_(d), and has the same meaning as that of R_(d)}}, aM_(c)-B_(a)-group (M_(c) and B_(a) are as defined above), aM_(c)-CO-group (M_(c) is as defined above), a M_(c)-CO—O-group (M_(c) isas defined above), a M_(c)O—CO-group (M_(c) is as defined above), aM_(c)R_(e)N-group (M_(c) and R_(e) are as defined above), aM_(c)-CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)O—CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO—NR_(e)′-group (M_(c), R_(e) and R_(d)′ are as definedabove), a M_(c)R_(e)N—C(═NR_(e)′)—NR_(e)″-group (M_(c), R_(e), R_(e)′and R_(e)″ are as defined above), a M_(c)-SO₂—NR_(e)-group (M_(c) andR_(e) are as defined above) or M_(c)R_(e)N—SO₂-group (M_(c) and R_(e)are as defined above), and R_(d) is as defined above];

-   (3) a Z₂ group:

a —N═C(Y_(a)) Y_(a)′-group (Y_(a) represents a hydrogen atom, or aC1-C10 alkyl group optionally substituted with a halogen atom, or aC1-C10 alkoxy group, and Y_(a)′ represents an oxy group, or a thiogroup, or an imino group optionally substituted C1-C10 alkyl group), a—Y_(b)—Y_(b)′—Y_(b)″-group (Y_(b) and Y_(b)″ are the same or different,and represent a methylene group, or an oxy group, or a thio group, or asulfinyl group, or an imino group optionally substituted with a C1-C10alkyl group, and Y_(b)′ represents a C1-C4 alkylene group optionallysubstituted with a halogen atom, or a C1-C4 alkylene group optionallyhaving an oxo group) or a —Y_(c)—O—Y_(c)′—O-group (Y_(c) and Y_(c)′ arethe same or different, and represent a C1-C10 alkylene group);

-   III. Q_(A)′ represents a (b)-group ((b) is as defined above), an    A₉-B₆—B_(c)-group [A₉ represents a substituent of the following A₇    group or A₈ group, B₆ represents a carbonyl group or a thiocarbonyl    group, and B_(c) represents an oxy group or a —N((O)_(m)R₁-group (m    represents 0 or 1, and R₁ is as defined above), provided that when    A₉ is a hydrogen atom, then B_(c) is not a sulfonyl group], an    A₇″—SO₂—B_(c)-group (A₇″ represents a substituent of the following    A₇″ group, and B_(c) is as defined above), an A₈-SO₂—B_(c)-group (A₈    represents a substituent of the following A₈ group, and B_(c) is as    defined above, provided that A₈ is not a hydrogen atom), a    R₁R₁′N—SO₂—B_(c)-group (R₁ is as defined above, R₁′ is the same as    or different from R₁, and has the same meaning as that of R₁ and    B_(c) is as defined above), a (b)-SO₂—B_(c)-group ((b) and B_(c) are    as defined above), an A₉′-B_(c)-group (A₉′ represents a substituent    of the following A₇′ group or A₈′ group, and B_(c) is as defined    above), a D₅-R₄—B_(c)-group (D₅ represents a substituent of the    following D₅ group, R₄ represents a C1-C10 alkylene group, and B_(c)    is as defined above), a M_(c)-B₃—B_(c)-group (B₃ represents a    carbonyl group, a thiocarbonyl group or a sulfonyl group, and M_(c)    and B_(c) are as defined above) or a M_(c)-B_(c)-group (M_(c) and    B_(c) are as defined above);-   (1) an A₇ group:

a C2-C10 alkenyl group optionally substituted with a halogen atom, aC2-C10 alkynyl group, a C3-C10 haloalkynyl group, a R₂—B₁—R₄-group (R₂and B₁ are as defined above, and R₄ is as defined above), a D₄-R₄-group(D₄ represents a substituent of the following D₄ group, and R₄ is asdefined above), a D₅-R₄-group (D₅ represents a substituent of thefollowing D₅ group, and R₄ is as defined above), a D₁-R₄-group {D₁represents a substituent of the following D₁ group, and R₄ is as definedabove}, a (b)-R₄-group ((b) is as defined above, and R₄ is as definedabove), a (c)-R₄-group ((c) is as defined above, and R₄ is as definedabove), a D₂-R₄-group {D₂ represents a substituent of the following D₂group, and R₄ is as defined above}, a D₃-R₄-group {D₃ represents asubstituent of the following D₃ group, and R₄ is as defined above}, anA₄-SO₂—R₄-group {A₄ represents a (b)-group ((b) is as defined above), a(c)-group ((c) is as defined above) or a R₁R₁′N-group (R₁ and R₁′ are asdefined above), and R₄ is as defined above} or an A₂-CO—R₄-group (A₂represents a substituent of the following A₂ group, and R₄ is as definedabove);

-   (2) an A₈ group: a hydrogen atom, or a C1-C10 alkyl group optionally    substituted with a halogen atom;-   (3) an A₇′ group: a C3-C10 alkenyl group optionally substituted with    a halogen atom, a C3-C10 alkynyl group optionally substituted with a    halogen atom, a C₂—B₁—R₄′-group (C₂ and B₁ are as defined above, and    R₄′ represents a C2-C10 alkylene group), a D₄-R₄′-group (D₄ and R₄′    are as defined above), a D₁-R₄′-group (D₁ and R₄′ are as defined    above), a (b)-R₄′-group ((b) and R₄′ are as defined above), a    (c)-R₄′-group ((c) and R₄′ are as defined above), a D₂-R₄-group (D₂    and R₄ are as defined above), a D₃-R₄′-group (D₃ and R₄′ are as    defined above) or an A₂-CO—R₄-group (A₂ and R₄ are as defined    above);-   (4) an A₈-group: a C1-C10 alkyl group or a C2-C10 haloalkyl group;-   (5) an A₇″-group: a C2-C10 alkenyl group, a C3-C10 alkenyl group    substituted with a halogen atom, a C3-C10 alkynyl group optionally    substituted with a halogen atom, a R₂—B₁—R₄′-group (R₂, B₁ and R₄′    are as defined above), a D₄-R₄′-group (D₄ and R₄′ are as defined    above), a D₅-R₄-group (D₅ and R₄ are as defined above), a    D₁-R₄′-group (D₁ and R₄″ are as defined above), a (b)-R₄′-group ((b)    and R₄′ are as defined above), a (c)-R₄′-group ((c) and R₄′ are as    defined above), a D₂-R₄-group (D₂ and R₄ are as defined above), a    NO₂—R₄-group (R₄ is as defined above) or an A₂-CO—R₄-group (A₂ and    R₄ are as defined above);-   (i) a D₄ group: a hydroxyl group or an A₁-O-group [A₁ represents a    R₃—(CHR₀)_(m)—(B₂—B₃)_(m)′-group {R₃ represents a hydrogen atom, or    a C1-C10 alkyl group optionally substituted with a halogen atom or a    R₂—B₁-group (R₂ and B₁ are as defined above), or a C2-C10 alkenyl    group, or a C2-C1 alkynyl group, R₀ represents a hydrogen atom,    C1-C10 alkyl group or a C2-C10 haloalkyl group, m is as defined    above, B₂ represents a single bond, an oxy group, a thio group or a    —N((O)_(n)R₁′-group (R₁′ is as defined above, and n represents 0 or    1), B₃ is as defined above, and m′ represents 0 or 1 and, when B₃ is    a sulfonyl group, m is 0, and R₃ is not a hydrogen atom}];-   (ii) a D₅ group: O═C(R₃) group (R₃ is as defined above), an    A₁-(O)_(n)—N═C(R₃)-group (A₁, n and R₃ are as defined above), an    R₁—B₀—CO—R₄—(O)_(n)—N═C(R₃)-group [R₁, R₄, n and R₃ are as defined    above, and B₀ represents an oxy group, a thio group or a    —N((O)_(m)R₁′)-group (R₁′ and m are as defined above)], a D₂-R₄—    (O)_(n)—N═C(R₃)-group (D₂, R₄, n and R₃ are as defined above) or a    R₁A₁N—N═C(R₃) group (R₁, A₁ and R₃ are as defined above);-   (iii) a D₁ group: a (R₁—(O)_(k)-)A₁N—(O)_(k)′-group (R₁ and A₁ are    as defined above, and k and k′ are the same or different, and    represent 0 or 1);-   (iv) a D₂ group: a cyano group, a R₁R₁′NC(═N—(O)_(n)-A₁-group (R₁,    R₁′, n and A₁ are as defined above), an A₁N═C(—OR₂)-group (A₁ and R₂    are as defined above) or a NH₂—CS-group.-   (v) a D₃ group: a nitro group or a R₁OSO₂-group (R₁ is as defined    above);-   (vi) an A₂ group:-   1) an A₃-B₄-group-   [A₃ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10    haloalkyl group, or a C2-C10 alkenyl group optionally substituted    with a halogen atom, or a C3-C10 alkynyl group optionally    substituted with a halogen atom, or a R_(a)—(R₄)_(m)-group (R_(a)    represents a phenyl group, a pyridyl group, a furyl group or a    thienyl group, optionally substituted with a halogen atom, a C1-C10    alkyl group, a C1-C10 alkoxy group or a nitro group, and R₄ and m    are as defined above), or a C1-C10 alkyl group substituted with a    (b)-R₄-group ((b) and R₄ are as defined above), a (c)-R₄-group ((c)    and R₄ are as defined above), a R₂—B₁—R₄-group (R₂, B₁ and R₄ are as    defined above), a D₄-R₄-group (D₄ and R₄ are as defined above), a    D₅-group (D₅ is as defined above), a D₁-R₄-group (D₁ and R₄ are as    defined above), a D₂-group (D₂ is as defined above), a D₃-R₄-group    (D₃ and R₄ are as defined above) or an A₄-SO₂—R₄-group {A₄ is as    defined above, and R₄ is as defined above},

B₄ represents an oxy group, a thio group or a —N((O)_(m)R₁)-group (R₁and m are as defined above), provided that when B₄ is a thio group, A₃is not a hydrogen atom];

-   2) a R₁—B₄—CO—R₄—B₄′-group (R₁, B₄ and R₄ are as defined above, B₄′    is the same as or different from B₄, and has the same meaning as    that of B₄ provided that when B₄ is a thio group, R₂ is not a    hydrogen atom) or a D₂-R₄—B₄-group (D₂, R₄ and B₄ are as defined    above);-   3) a R₂—SO₂—NR₁-group (R₂ is as defined above provided that a    hydrogen atom is excluded, and R₁ is as defined above),-   4) a (b)-group ((b) is as defined above);-   5) a (c)-group ((c) is as defined above); or-   6) a R₁A₁N—NR₁′-group (R₁, A₁ and R₁′ are as defined above);-   IV. K_(a) represents a hydrogen atom, a halogen atom or a C1-C10    alkyl group, L_(a) represents a hydrogen atom, a C1-C10 alkyl group    or a M_(b)-group (M_(b) is as defined above), or K_(a) and L_(a) may    form a C1-C10 alkylene group, provided that when an A ring is a    benzene ring, p is 2, 3 or 4 in the case that q is 0; and

the “as defined above” in the same symbol between a plurality ofsubstituents indicates that the plurality of substituents independentlyrepresent the same meaning as that described above and, between theplurality of substituents, a selection range of selected substituents isthe same, while the selected substituents may be the same or differentas far as they are selected in the range];

6. A 2H-pyran-2-one compound represented by the formula (VI):

[wherein

-   I. A represents a benzene ring or a pyridine ring;-   II. In (X_(c))_(p), X_(c) is a substituent on a carbon atom, and    represents a hydroxyl group, or a halogen atom, or a C1-C10 alkyl    group optionally substituted with a halogen atom or a C1-C10 alkoxy    group, or a C2-C10 alkenyl group, or a R′—S(O)_(l)-group (R′    represents a C1-C10 alkyl group, and l represents 0, 1 or 2), or a    cyano group, or a C1-C10 alkoxycarbonyl group, or an aminocarbonyl    group, or a (R′)₂N-group (R′ is as defined above), or a    R′CO—NH-group (R′ is as defined above), or a nitro group, or a    C1-C10 alkoxy group, or a RB-group (R represents a C1-C10 haloalkyl    group, and B represents an oxy group or a thio group), p represents    0, 1, 2, 3 or 4 and, when p is 2 or more, X_(c)'s are the same or    different;-   III. In (Y_(c))_(q), Y_(c) is a substituent on a carbon atom, and    represents a substituent of the following X₃ group or Y₃ group, q    represents 0, 1, 2, 3, 4 or 5, when q is 2 or more, Y_(c)'s are the    same or different and, when q is 2 or more, the adjacent two same or    different Y_(c)'s constitute a group of a Z₃ group, and may be fused    with an A ring;-   (1) a X₃ group:

a M_(a)-group [M_(a) represents a R_(b)-group (R_(b) represents a C1-C10alkyl group substituted with a halogen atom), a halogen atom, a nitrogroup, a cyano group, a hydroxy group, a R_(c)—B_(a)—R_(d)-group (R_(c)represents a C1-C10 alkyl group optionally substituted with a halogenatom, B_(a) represents an oxy group, a thio group, a sulfinyl group or asulfonyl group, and R_(d) represents a single bond or a C1-C10 alkylenegroup), a HOR_(d)-group (R_(d) is as defined above), aR_(e)—CO—R_(d)-group (R_(e) represents a hydrogen atom, or a C1-C10alkyl group optionally substituted with a halogen atom, and R_(d) is asdefined above), a R_(e)—CO—O—R_(d)-group (R_(e) and R_(d) are as definedabove), a R_(e)O—CO—R_(d)-group (R_(e) and R_(d) are as defined above),a HO—CO—CH═CH-group, a R_(e)R_(e)′N—R_(d)-group (R_(e) and R_(e)′ arethe same or different, R_(e) is as defined above, R_(e)′ has the samemeaning as that of R_(e), and R_(d) is as defined above), aR_(e)—CO—NR_(e)′—R_(d)-group (R_(e), R_(e)′ and R_(d) are as definedabove), a R_(b)O—CO—N(R_(e))—R_(d)-group (R_(b), R_(e) and R_(d) are asdefined above), a R_(e)R_(e)′N—CO—R_(d)-group (R_(e), R_(e)′ and R_(d)are as defined above), a R_(e)R_(e)′N—CO—NR_(e)″—R_(d)-group (R_(e),R_(e)′ and R_(e)″ are the same or different, R_(e) and R_(e)′ are asdefined above, R_(e)″ has the same meaning as that of R_(e), and R_(d)is as defined above), a R_(e)R_(e)′N—C(═NR_(e)″)—NR_(e)′″—R_(d)-group(R_(e), R_(e)′, R_(e)″ and R_(e)′″ are the same or different, R_(e),R_(e)′ and R_(e)″ are as defined above, R_(e)′″ has the same meaning asthat of R_(e), and R_(d) is as defined above), aR_(b)—SO₂—NR_(e)—R_(d)-group (R_(b), R_(e) and R_(d) are as definedabove), a R_(e)R_(e)′N—SO₂—R_(d)-group (R_(e), R_(e)′ and R_(d) are asdefined above), a C2-C10 alkenyl group or a C2-C10 alkynyl group],provided that when A represents a benzene ring, then a hydroxy group, ora halogen atom, or a C1-C10 alkyl group optionally substituted with ahalogen atom or a C1-C10 alkoxy group, or a C2-C10 alkenyl group, or aR′—S(O)_(l)-group (R′ represents a C1-C10 alkyl group, and l represents0, 1 or 2), or a cyano group, or a C1-C10 alkoxycarbonyl group, or anaminocarbonyl group, or a (R′)₂N-group (R′ is as defined above), or aR′CO—NH-group (R′ is as defined above), or a nitro group or a C1-C10alkoxy group is excluded;

-   (2) a Y₃ group:

a M_(b)-R_(d)-group [M_(b) represents a M_(c)-group {M_(c) represents aM_(d)-R_(d)′-group {M_(d) represents a phenyl group optionallysubstituted with a M_(a)-group (M_(a) is as defined above), or a pyridylgroup optionally substituted with a M_(a)-group (M_(a) is as definedabove), or a naphthyl group optionally substituted with a M_(a)-group(M_(a) is as defined above), or

a (b)-group {in (b), G₁, G₂, G₄ and G₅ represent a methylene group whichis connected to an adjacent atom with a single bond, and may besubstituted with a methyl group, or a methine group which is connectedto an adjacent atom with a double bond, and may be substituted with amethyl group, and G₃ represents a single bond, or a double bond, or aC1-C10 alkylene group optionally substituted with a methyl group, an oxygroup, a thio group, a sulfinyl group, a sulfonyl group or a —NR₁-group{R₁ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10alkyl group substituted with a halogen atom or a R₂—B₁-group (R₂represents a C1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10alkynyl group, and B₁ represents an oxy group, a thio group, a sulfinylgroup or a sulfonyl group) or a C3-C10 alkenyl group, or a C3-C10alkynyl group), or a C2-C10 alkenylene group optionally substituted witha methyl group, an oxy group, a thio group, a sulfinyl group, a sulfonylgroup or a —NR₁-group (R₁ is as defined above)},

a (c)-group (in (c), J₁, J₂ and J₃ are the same or different, andrepresent a methine group optionally substituted with a methyl group, ora nitrogen atom),

a (d)-group (l is 2, 3 or 4, and B_(b) represents an oxy group or a thiogroup)or

an (e)-group (l and B_(b) are as defined above), R_(d)′ is the same asor different from R_(d), and has the same meaning as that of R_(d)}}, aM_(c)-B_(a)-group (M_(c) and B_(a) are as defined above), aM_(c)-CO-group (M_(c) is as defined above), a M_(c)-CO—O-group (M_(c) isas defined above), a M_(c)O—CO-group (M_(c) is as defined above), aM_(c)R_(e)N-group (M_(c) and R_(e) are as defined above), aM_(c)-CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)O—CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO—NR_(e)′-group (M_(c), R_(e) and R_(e)′ are as definedabove), a M_(c)R_(e)N—C(═NR_(e)′)—NR_(e)″-group (M_(c), R_(e), R_(e)′and R_(e)″ are as defined above), a M_(c)-SO₂—NR_(e)-group (M_(c) andR_(e) are as defined above) or a M_(c)R_(e)N—SO₂-group (M_(c) and R_(e)are as defined above), and R_(d) is as defined above], provided thatwhen P is 0, then a morpholino group, or a phenyl group, or a phenoxygroup substituted with a trifluoromethyl group, or a phenoxy groupsubstituted with single or plural halogen atoms is excluded;

-   (3) a Z₃ group:-   a —N═C(Y_(a))—Y_(a)′-group (Y_(a) represents a hydrogen atom, or a    C1-C10 alkyl group optionally substituted with a halogen atom, or a    C1-C10 alkoxy group, and Y_(a)′ represents an oxy group, or a thio    group, or an imino group optionally substituted with a C1-C10 alkyl    group), a —Y_(b)—Y_(b)′—Y_(b)″-group (Y_(b) and Y_(b)″ are the same    or different, and represent a methylene group, or an oxy group, or a    thio group, or a sulfinyl group, or an imino group optionally    substituted with a C1-C10 alkyl group, and Y_(b)′ represents a C1-C4    alkylene group optionally substituted with a halogen atom, or a    C1-C4 alkylene group optionally having an oxo group) or a    —Y_(c)—O—Y_(c)′—O-group (Y_(c) and Y_(c)′ are the same or different,    and represent a C1-C10 alkylene group), provided that when p is 0,    then Y_(c) is not fused with an A ring to form a benzo[1,3]dioxol    ring;-   IV. K_(a) represents a hydrogen atom, a halogen atom or a C1-C10    alkyl group, L_(a) represents a hydrogen atom, a C1-C10 alkyl group    or a M_(b)-group (M_(b) is as defined above), or K_(a) and L_(a) may    form a C1-C10 alkylene group, provided that when an A ring is a    benzene ring, then q is not 0 and, when an A ring is a benzene ring    or a pyridine ring, then p and q are not 0 at the same time, in    either case; and

the “as defined above” in the same symbol between a plurality ofsubstituents indicates that the plurality of substituents independentlyrepresent the same meaning as that described above, and between theplurality of substituents, a selection range of selected substituents isthe same, while the selected range may be the same or different as faras they are selected in the range];

7. A I type collagen gene transcription suppressing composition, whichcomprises a 2H-pyran-2-one compound represented by the formula (VII):

[wherein X_(I) represents a C2-C4 alkenyl group, a C2-C4 alkynyl group,a R_(I)—S(O)_(l)-group (R_(I) represents a C1-C4 alkyl group, and lrepresents an integer of 0 to 2), a cyano group, a carboxy group, aC1-C4 alkoxycarbonyl group, a (R_(I))₂N-group (R_(I) is as definedabove), a R_(I)—CO—NH-group (R_(I) is as defined above), aR_(I)O—CO—NH-group (R_(I) is as defined above), a R_(I)NH—CO—NH-group(R_(I) is as defined above) or a (R_(I)′)₂N—CO-group (R_(I)′ representsa hydrogen atom or a C1-C4 alkyl group), X₁′ represents a halogen atom,or a C1-C4 alkyl group optionally substituted with a halogen atom or aC1-C4 alkoxy group, or a nitro group, or a C1-C4 alkoxy group, or aRB-group (B represents an oxygen atom or a sulfur atom, and R representsa C1-C4 alkyl group substituted with a halogen atom), k represents 0 or1, k′ represents an integer of 0 to 4, when k is 0, k′ is an integer of2 to 4 and, when k′ is 2 to 4, X_(I)′'s may be different, and r_(I) is aC1-C4 alkyl group, a C2-C4 alkenyl group or a C2-C4 alkynyl group], anda inert carrier;

8. A 2H-pyran-2-one compound represented by the formula (VIII):

[wherein X_(I) represents a C2-C4 alkenyl group, a C2-C4 alkynyl group,a R_(I)—S(O)_(l)-group (R_(I) represents a C1-C4 alkyl group, and lrepresents an integer of 0 to 2), a cyano group, a carboxy group, aC1-C4 alkoxycarbonyl group, a (R_(I))₂N-group (R_(I) is as definedabove), a R_(I)—CO—NH-group (R_(I) is as defined above), aR_(I)O—CO—NH-group (R_(I) is as defined above), a R_(I)NH—CO—NH-group(R_(I) is as defined above) or (R_(I)′)₂N—CO-group (R_(I)′ represents ahydrogen atom or a C1-C4 alkyl group), X_(I)″ represents a halogen atom,or a C1-C4 alkyl group optionally substituted with a halogen atom or aC1-C4 alkoxy group, or a nitro group, or a C2-C4 alkoxy group, or aRB-group (B represents an oxygen atom or a sulfur atom, and R representsa C1-C4 alkyl group substituted with a halogen atom), k represents 0 or1, k′ represents an integer of 0 to 4, when k is 0, k′ is an integer of2 to 4 and, when k′ is 2 to 4, X_(I)″'s may be different, and r_(I) is aC1-C4 alkyl group, a C2-C4 alkenyl group or a C2-C4 alkynyl group];

9. A 2H-pyran-2-one compound represented by the formula (IX):

(wherein X_(I)′″ represents a C2-C4 alkenyl group, a C2-C4 alkynylgroup, a carboxy group, a C2-C4 alkoxycarbonyl group or a(R_(II))₂N-group (R_(II) represents a C2-C4 alkyl group), X_(I)″represents a halogen atom, or a C1-C4 alkyl group optionally substitutedwith a halogen atom or a C1-C4 alkoxy group, or a nitro group, or aC2-C4 alkoxy group, or a RB-group (B represents an oxygen atom or asulfur atom, and R represents a C1-C4 alkyl group substituted with ahalogen atom), k represents 0 or 1, k″ represents an integer of 0 to 2,when k is 0, k″ is 2 and, when k″ is 2, X″'s are different];

10. A I type collagen gene transcription suppressing composition, whichcomprises a 2H-1-benzopyran-2-one compound represented by the formula(X):

[wherein

-   I. A represents a benzene ring or a pyridine ring;-   II. In (X_(d))_(p), X_(d) is a substituent on a carbon atom, and    represents a methoxy group or an ethoxy group, p represents 0, 1, 2,    3 or 4 and, when p is 2 or more, X_(d)'s are the same or different;-   III. In (Y_(d))_(q), Y_(d) is a substituent on a carbon atom, and    represents a substituent of the following X₄ group or Y₄ group, q    represents 0, 1, 2, 3, 4 or 5, when q is 2 or more, Y_(d)'s are the    same or different and, q is 2 or more, the adjacent two same or    different Y_(d)'s constitute a group of a Z₄ group, and may be fused    with an A ring;-   (1) a X₄ group:

a M_(a)-group [M_(a) represents a R_(b)-group (R_(b) represents a C1-C10alkyl group optionally substituted with a halogen atom), a halogen,atom, a nitro group, a cyano group, a hydroxyl group, aR_(c)—B_(a)—R_(d)-group (R_(c) represents a C1-C10 alkyl groupoptionally substituted with a halogen atom, B_(a) represents an oxygroup, a thio group, a sulfinyl group or a sulfonyl group, and R_(d)represents a single bond or a C1-C10 alkylene group), a HOR_(d)-group(R_(d) is as defined above), a R_(e)—CO—R_(d)-group (R_(e) represents ahydrogen atom, or a C1-C10 alkyl group optionally substituted with ahalogen atom, and R_(d) is as defined above), a R_(e)—CO—O—R_(d)-group(R_(e) and R_(d) are as defined above), a R_(e)O—CO—R_(d)-group (R_(e)and R_(d) are as defined above), a HO—CO—CH═CH-group, aR_(e)R_(e)′N—R_(d)-group (R_(e) and R_(e)′ are the same or different,R_(e) is as defined above, R_(e)′ has the same meaning as that of R_(e),and R_(d) is as defined above), a R_(e)—CO—NR_(e)′—R_(d)-group (R_(e),R_(e)′ and R_(d) are as defined above), a R_(b)O—CO—N(R_(e))—R_(d)-group(R_(b), R_(e) and R_(d) are as defined above), aR_(e)R_(e)′N—CO—R_(d)-group (R_(e), R_(e)′ and R_(d) are as definedabove), a R_(e)R_(e)′N—CO—NR_(e)″—R_(d)-group (R_(e), R_(e)′ and R_(e)″are the same or different, R_(e) and R_(e)′ are as defined above, R_(e)″has the same meaning as that of R_(e), and R_(d) is as defined above), aR_(e)R_(e)′N—C(═NR_(e)″)—NR_(e)′″—R_(d)-group (R_(e), R_(e)′, R_(e)″ andR_(e)′″ are the same or different, R_(e), R_(e)′ and R_(e)′″ are asdefined above, R_(e)′″ has the same meaning as that of R_(e), and R_(d)is as defined above), a R_(b)—SO₂—NR_(e)—R_(d)-group (R_(b), R_(e) andR_(d) are as defined above), a R_(e)R_(e)′N—SO₂—R_(d)-group (R_(e),R_(e)′ and R_(d) are as defined above), a C2-C10 alkenyl group or aC2-C10 alkynyl group], provided that when A represents a benzene ring,then a methoxy group and an ethoxy group are excluded;

-   (2) a Y₄ group:-   a M_(b)-R_(d)-group [M_(b) represents a M_(c)-group {M_(c)    represents a M_(d)-R_(d)′-group {M_(d) represents a phenyl group    optionally substituted with a M_(a)-group (M_(a) is as defined    above), or a pyridyl group optionally substituted with a M_(a)-group    (M_(a) is as defined above), or a naphthyl group optionally    substituted with a M_(a)-group (M_(a) is as defined above), or

a (b)-group {in (b), G₁, G₂, G₄ and G₅ represent a methylene group whichis connected to an adjacent atom with a single bond, and may besubstituted with a methyl group, or a methine group which is connectedto an adjacent atom with a double bond, and may be substituted with amethyl group, and G₃ represents a single bond, or a double bond, or aC1-C10 alkylene group optionally substituted with a methyl group, an oxygroup, a thio group, a sulfinyl group, a sulfonyl group or a —NR₁-group{R₁ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10alkyl group optionally substituted with a halogen atom or a R₂—B₁-group(R₂ represents a C1-C10 alkyl group, a C3-C10 alkenyl group or C3-C10alkynyl group, and B₁ represents an oxy group, a thio group, a sulfinylgroup or a sulfonyl group), or a C3-C10 alkenyl group, or a C3-C10alkynyl group} or a C2-C10 alkenylene group optionally substituted witha methyl group, an oxy group, a thio group, a sulfinyl group, a sulfonylgroup or a —NR₁-group (R₁ is as defined above)},

a (c)-group (in (c), J₁, J₂ and J₃ are the same or different, andrepresent a methine group optionally substituted with a methyl group, ora nitrogen atom),

a (d)-group (l is 2, 3 or 4, and B_(b) represents an oxy group or a thiogroup)or

an (e)-group (l and B_(b) are as defined above), R_(d)′ is the same asor different from R_(d), and has the same meaning as that of R_(d)}}, aM_(c)-B_(a)-group (M_(c) and B_(a) are as defined above), aM_(c)-CO-group (M_(c) is as defined above), a M_(c)-CO—O-group (M_(c) isas defined above), a M_(c)O—CO-group (M_(c) is as defined above), aM_(c)R_(e)N-group (M_(c) and R_(e) are as defined above), aM_(c)-CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)O—CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO—NR_(e)′-group (M_(c), R_(e) and R_(e)′ are as definedabove), a M_(c)R_(e)N—C(═NR_(e)′)—NR_(e)″-group (M_(c), R_(e), R_(e)′and R_(e)″ are as defined above), a M_(c)-SO₂—NR_(e)-group (M_(c) andR_(e) are as defined above) or a M_(c)R_(e)N—SO₂-group (M_(c) and R_(e)are as defined above), and R_(d) is as defined above];

-   (3) a Z₄ group:-   a —N═C(Y_(a))—Y_(a)′-group (Y_(a) represents a hydrogen atom, or a    C1-C10 alkyl group optionally substituted with a halogen atom, or a    C1-C10 alkoxy group, and Y_(a)′ represents an oxy group, or a thio    group, or an imino group optionally substituted with a C1-C10 alkyl    group), a —Y_(b)—Y_(b)′—Y_(b)″-group (Y_(b) and Y_(b)″ are the same    or different, a methylene group, or an oxy group, or a thio group,    or a sulfinyl group, or an imino group optionally substituted with a    C1-C10 alkyl group, and Y_(b)′ represents a C1-C4 alkylene group    optionally substituted with a halogen atom, or a C1-C4 alkylene    group optionally having an oxo group) or a —Y_(c)—O—Y_(c)′—O-group    (Y_(c) and Y_(c)′ are the same or different, and represent a C1-C10    alkylene group);-   IV. Q_(A) represents a hydroxyl group, a (b) group ((b) is as    defined above), an A₉-B₆—B_(c)-group [A₉ represents a substituent of    the following A₇ group or A₈ group, B₆ represents a carbonyl group    or a thiocarbonyl group, and B_(c) represents an oxy group or a    —N((O)_(m)R₁)-group (m represents 0 or 1, and R₁ is as defined    above), provided that when A₉ is a hydrogen atom, then B_(c) is not    a sulfonyl group], an A₇″-SO₂—B_(c)-group (A₇″ represents a    substituent of the following A₇″ group, and B_(c) is as defined    above), an A₈-SO₂—B_(c)-group (A₈ represents a substituent of the    following A₈ group, and B_(c) is as defined above, provided that A₈    is not a hydrogen atom), a R₁R₁′N—SO₂—B_(c)-group (R₁ is as defined    above, R₁′ is the same as or different from R₁, and has the same    meaning as that of R₁, and B_(c) is as defined above), a    (b)-SO₂—B_(c)-group ((b) and B_(c) are as defined above), an    A₉′-B_(c)-group (A₉′ represents a substituent of the following A₇′    group or A₈′ group, and B_(c) is as defined above), a    D₅-R₄—B_(c)-group (D₅ represents a substituent of the following D₅    group, R₄ represents a C1-C10 alkylene group, and B_(c) is as    defined above), a M_(c)-B₃—B_(c)-group (B₃ represents a carbonyl    group, a thiocarbonyl group or a sulfonyl group, and M_(c) and B_(c)    are as defined above) or a M_(c)-B_(c)-group (M_(c) and B_(c) are as    defined above);-   (1) an A₇ group:-   a C2-C10 alkenyl group optionally substituted with a halogen atom, a    C2-C10 alkynyl group, a C3-C10 haloalkynyl group, a R₂—B₁—R₄-group    (R₂ and B₁ are as defined above, and R₄ is as defined above), a    D₄-R₄-group (D₄ represents a substituent of the following D₄ group,    and R₄ is as defined above), a D₅-R₄-group (D₅ represents a    substituent of the following D₅ group, and R₄ is as defined above),    a D₁-R₄-group {D₁ represents a substituent of the following D₁    group, and R₄ is as defined above}, a (b)-R₄-group ((b) is as    defined above, and R₄ is as defined above), a (c)-R₄-group ((c) is    as defined above, and R₄ is as defined above), a D₂-R₄-group {D₂    represents a substituent of the following D₂ group, and R₄ is as    defined above}, a D₃-R₄-group {D₃ represents a substituent of the    following D₃ group, and R₄ is as defined above}, an A₄-SO₂—R₄-group    {A₄ represents a (b)-group ((b) is as defined above), a (c)-group    ((c) is as defined above) or a R₁R₁′N-group (R₁ and R₁′ are as    defined above), and R₄ is as defined above} or an A₂-CO—R₄-group (A₂    represents a substituent of the following A₂ group, and R₄ is as    defined above);-   (2) an A₈ group: a hydrogen atom, or a C1-C10 alkyl group optionally    substituted with a halogen atom;-   (3) an A₇′ group: a C3-C10 alkenyl group optionally substituted with    a halogen atom, a C3-C10 alkynyl group optionally substituted with a    halogen atom, a R₂—B₁—R₄′-group (R₂ and B₁ are as define above, and    R₄′ represents a C2-C4 alkylene group), a D₄-R₄′-group (D₄ and R₄′    are as defined above), a D₁-R₄′-group (D₁ and R₄′ are as defined    above), a (b)-R₄′-group ((b) and R₄′ are as defined above), a    (c)-R₄′-group ((c) and R₄′ are as defined above), a D₂-R₄-group (D₂    and R₄ are as defined above), a D₃-R₄′-group (D₃ and R₄′ are as    defined above) or an A₂-CO—R₄-group (A₂ and R₄ are as defined    above);-   (4) an A₈′ group: a C1-C10 alkyl group or a C2-C10 haloalkyl group;-   (5) an A₇″ group: a C2-C10 alkenyl group, a C3-C10 alkenyl group    substituted with a halogen atom, a C3-C10 alkynyl group optionally    substituted with a halogen atom, a R₂—B₁—R₄′-group (R₂, B₁ and R₄′    are as defined above), a D₄-R₄′-group (D₄ and R₄′ are as defined    above), a D₅-R₄-group (D₅ and R₄ are as defined above), a    D₁-R₄′-group (D₁ and D₄′ are as defined above), a (b)-R₄′-group ((b)    and R₄′ are as defined above), a (c)-R₄′-group ((c) and R₄′ are as    defined above), a D₂-R₄-group (D₂ and R₄ are as defined above), a    NO₂—R₄-group (R₄ is as defined above) or an A₂-CO—R₄-group (A₂ and    R₄ are as defined above);-   (i) a D₄ group: a hydroxy group or an A₁-O-group [A₁ represents a    R₃—(CHR₀)_(m)—(B₂—B₃)_(m)′-group {R₃ represents a hydrogen atom, or    a C1-C10 alkyl group optionally substituted with a halogen atom or a    R₂—B₁-group (R₂ and B₁ are as defined above), or a C2-C10 alkenyl    group, or C2-C10 alkynyl group, R₀ represents a hydrogen atom, a    C1-C10 alkyl group or a C2-C10 haloalkyl group, m is as defined    above, B₂ represents a single bond, an oxy group, a thio group or a    —N((O)_(m)R₁′)-group (R₁′ is as defined above, and n represents 0 or    1), B₃ is as defined above, m′ represents 0 or 1 and, when B₃ is a    sulfonyl group, then m is 0, and R₃ is not a hydrogen atom}];-   (ii) a D₅ group: an O═C(R₃)-group (R₃ is as defined above), an    A₁-(O)_(n)—N═C(R₃)-group (A₁, n and R₃ are as defined above), a    R₁—B₀—CO—R₄—(O)_(n)—N═C(R₃)-group [R₁, R₄, n and R₃ are as defined    above, and B₀ represents an oxy group, a thio group or a    —N((O)_(m)R₁′)-group (R₁′ and m are as defined above)], a    D₂-R₄—(O)_(n)—N═C(R₃)-group (D₂, R₄, n and R₃ are as defined above)    or a R₁A₁N—N═C(R₃)-group (R₁, A₁ and R₃ are as defined above);-   (iii) a D₁ group: a (R₁—(O)_(k)-)A₁N—(O)_(k)′-group (R₁ and A₁ are    as defined above, and k and k′ are the same or different, and    represent 0 or 1);-   (iv) a D₂ group: a cyano group, a R₁R₁′NC(═N—(O)_(n)-A₁)-group (R₁,    R₁′, n and A₁ are as defined above), an A₁N═C(—OR₂)-group (A₁ and R₂    are as defined above) or a NH₂—CS-group;-   (v) a D₃ group: a nitro group or a R₁OSO₂-group (R₁ is as defined    above);-   (vi) an A₂ group:-   1) an A₃-B₄-group-   [A₃ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10    haloalkyl group, or a C2-C10 alkenyl group optionally substituted    with a halogen atom, or a C3-C10 alkynyl group optionally    substituted with a halogen atom, or a R_(a)—(R₄)_(m)-group (R_(a)    represents a phenyl group, a pyridinyl group, a furyl group or a    thienyl group, optionally substituted with a halogen atom, a C1-C10    alkyl group, a C1-C10 alkoxy group or a nitro group, and R₄ and m    are as defined above), or a C1-C10 alkyl group substituted with a    (b)-R₄-group ((b) and R₄ are as defined above), a (c)-R₄-group ((c)    and R₄ are as defined above), a R₂—B₁—R₄-group (R₂, B₁ and R₄ are as    defined above), a D₄-R₄-group (D₄ and R₄ are as defined above), a    D₅-group (D₅ is as defined above), a D₁-R₄-group (D₁ and R₄ are as    defined above), a D₂-group (D₂ is as defined above), a D₃-R₄-group    (D₃ and R₄ are as defined above) or an A₄-SO₂—R₄-group {A₄ is as    defined above, and R₄ is as defined above},

B₄ represents an oxy group, a thio group or a —N((O)_(m)R₁)-group (R₁and m are as defined above), provided that when B₄ is a thio group, thenA₃ is not a hydrogen atom];

-   2) a R₁—B₄—CO—R₄—B₄′-group (R₁, B₄ and R₄ are as defined above, B₄′    is the same as or different from B₄, and has the same meaning as    that of B₄, provided that when B₄ is a thio group, then R₂ is not a    hydrogen atom) or a D₂-R₄—B₄-group (D₂, R₄ and B₄ are as defined    above);-   3) a R₂—SO₂—NR₁-group (R₂ is as defined above, provided that a    hydrogen atom is excluded, and R₁ is as defined above),-   4) a (b)-group ((b) is as defined above);-   5) a (c)-group ((c) is as defined above) or-   6) a R₁A₁N—NR₁′-group (R₁, A₁ and R₁′ are as defined above);-   V. M_(a)′ is the same as or different from M_(a), and has the same    meaning as that of M_(a), and r represents 0, 1, 2, 3 or 4, provided    that when an A ring is a benzene ring, in case that q and r are 0,    then p is 2, 2, 3 or 4; and

the “as defined above” in the same symbol between a plurality ofsubstituent indicates that the plurality of the substituentsindependently represent the same meaning as that of described above and,between the plurality of substituents, a selection range of the selectedsubstituents is the same, while the selected substituents may be thesame or different as far as they are selected in the range]; and aninert carrier;

11. A 2H-1-benzopyran-2-one compound represented by the formula (XI):

[wherein

-   I. A represents a benzene ring or a pyridine ring;-   II. In (X_(d))_(p), X_(d) is a substituent on a carbon atom, and    represents a methoxy group or an ethoxy group, p represents 0, 1, 2,    3 or 4 and, when p is 2 or more, X_(d)'s are the same or different;-   III. In (Y_(d))_(q), Y_(d) is a substituent on a carbon atom, and    represents a substituent of the following X₄ group or Y₄ group, q    represents 0, 1, 2, 3, 4 or 5, when q is 2 or more, Y_(d)'s are the    same or different and, when q is 2 or more, the adjacent two same or    different Y_(d)'s constitute a group of a Z₄ group, and may be fused    with an A ring;-   (1) a X₄ group:-   a M_(a)-group [M_(a) represents a R_(b)-group (R_(b) represents a    C1-C10 alkyl group optionally substituted with a halogen atom), a    halogen atom, a nitro group, a cyano group, a hydroxy group, a    R_(c)—B_(a)—R_(d)-group (R_(c) represents a C1-C10 alkyl group    optionally substituted with a halogen atom, B_(a) represents an oxy    group, a thio group, a sulfinyl group or a sulfonyl group, and R_(d)    represents a single bond or a C1-C10 alkylene group), a    HOR_(d)-group (R_(d) is as defined above), a R_(e)—CO—R_(d)-group    (R_(e) represents a hydrogen atom, or a C1-C10 alkyl group    optionally substituted with a halogen atom, and R_(d) is as defined    above), a R_(e)—CO—O—R_(d)-group (R_(e) and R_(d) are as defined    above), a R_(e)O—CO—R_(d)-group (R_(e) and R_(d) are as defined    above), a HO—CO—CH═CH-group, a R_(e)R_(e)′N—R_(d)-group (R_(e) and    R_(e)′ are the same or different, R_(e) is as defined above, R_(e)′    has the same meaning as that of R_(e), and R_(d) is as defined    above), a R_(e)—CO—NR_(e)′—R_(d)-group (R_(e), R_(e)′ and R_(d) are    as defined above), a R_(b)O—CO—N(R_(e))—R_(d)-group (R_(b), R_(e)    and R_(d) are as defined above), a R_(e)R_(e)′N—CO—R_(d)-group    (R_(e), R_(e)′ and R_(d) are as defined above), a    R_(e)R_(e)′N—CO—NR_(e)″—R_(d)-group (R_(e), R_(e)′ and R_(e)″ are    the same or different, R_(e) and R_(e)′ are as defined above, R_(e)″    has the same meaning as that of R_(e), and R_(d) is as defined    above), a R_(e)R_(e)′N—C(═NR_(e)″)—NR_(e)′″—R_(d)-group (R_(e),    R_(e)′, R_(e)″ and R_(e)′″ are the same or different, R_(e), R_(e)′    and R_(e)″ are as defined above, R_(e)′″ has the same meaning as    that of R_(e), and R_(d) is as defined above), a    R_(b)—SO₂—NR_(e)—R_(d)-group (R_(b), R_(e) and R_(d) are as defined    above), a R_(e)R_(e)′N—SO₂—R_(d)-group (R_(e), R_(e)′ and R_(d) are    as defined above), a C2-C10 alkenyl group or a C2-C10 alkynyl    group], provided that when A represents a benzene ring, then a    methoxy group and an ethoxy group are excluded;-   (2) Y₄ group:-   a M_(b)-R_(d)-group [M_(b) represents a M_(c)-group {M_(c)    represents a M_(d)-R_(d)′-group {M_(d) represents a phenyl group    optionally substituted with a M_(a)-group (M_(a) is as defined    above), a pyridyl group optionally substituted with a M_(a)-group    (M_(a) is as defined above), or a naphthyl group optionally    substituted with a M_(a)-group (M_(a) is as defined above), or

a (b)-group {in (b), G₁, G₂, G₄ and G₅ represent a methylene group whichis connected to an adjacent atom with a single bond, and may besubstituted with a methyl group, or a methine group which is connectedto an adjacent atom with a double bond, and may be substituted with amethyl group, and G₃ represents a single bond, or a double bond, or aC1-C10 alkylene group optionally substituted with a methyl group, an oxygroup, a thio group, a sulfinyl group, a sulfonyl group or a —NR₁-group{R₁ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10alkyl group substituted with a halogen atom or a R₂—B₁-group (R₂represents a C1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10alkynyl group, and B₁ represents an oxy group, a thio group, sulfinylgroup or a sulfonyl group), or a C3-C10 alkenyl group, or a C3-C10alkynyl group}, or a C2-C10 alkenylene group optionally substituted witha methyl group, an oxy group, a thio group, a sulfinyl group, a sulfonylgroup or a —NR₁-group (R₁ is as defined above)},

a (c)-group (in (c), J₁, J₂, and J₃ are the same or different and,represent a methine group optionally substituted with a methyl group, ora nitrogen atom),

a (d)-group (l is 2, 3 or 4, and B_(b) represents an oxy group or a thiogroup) or

an (e)-group (l and B_(b) are as defined above), R_(d)′ is the same asor different from R_(d), and has the same meaning as that of R_(d)}}, aM_(c)-B_(a)-group (M_(c) and B_(a) are as defined above), aM_(c)-CO-group (M_(c) is as defined above), a M_(c)-CO—O-group (M_(c) isas defined above), a M_(c)O—CO-group (M_(c) is as defined above), aM_(c)R_(e)N-group (M_(c) and R_(e) are as defined above), aM_(c)-CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)O—CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO—NR_(e)′-group (M_(c), R_(e) and R_(e)′ are as definedabove), a M_(c)R_(e)N—C(═NR_(e)′)—NR_(e)″-group (M_(c), R_(e), R_(e)′and R_(e)″ are as defined above), a M_(c)-SO₂—NR_(e)-group (M_(c) andR_(e) are as defined above) or a M_(c)R_(e)N—SO₂-group (M_(c) and R_(e)are as defined above), and R_(d) is as defined above];

-   (3) a Z₄ group:-   a —N═C(Y_(a))—Y_(a)′-group (Y_(a) represents a hydrogen atom, or    C1-C10 alkyl group optionally substituted with a halogen atom, or a    C1-C10 alkoxy group, and Y_(a)′ represents an oxy group, or a thio    group, or an imino group optionally substituted with a C1-C10 alkyl    group), a —Y_(b)—Y_(b)′-Y_(b)″-group (Y_(b) and Y_(b)′ are the same    or different, and represent a methylene group, or an oxy group, or a    thio group, or a sulfinyl group, or an imino group optionally    substituted with a C1-C10 alkyl group, Y_(b)′ represents a C1-C4    alkylene group optionally substituted with a halogen atom, or a    C1-C4 alkylene group optionally having an oxo group) or a    —Y_(c)—O—Y_(c)′—O-group (Y_(c) and Y_(c)′ are the same or different,    and a C1-C10 alkylene group);-   IV. Q_(A)′ represents a (b)-group ((b) is as defined above), an    A₉-B₆—B_(c)-group [A₉ represents a substituent of the following A₇    group or A₈ group, B₆ represents a carbonyl group or a thiocarbonyl    group, B_(c) represents an oxy group or a —N((O)_(m)R₁)-group (m    represents 0 or 1, and R₁ is as defined above), provided that when    A₉ is a hydrogen atom, then B_(c) is not a sulfonyl group], an    A₇″-SO₂—B_(c)-group (A₇″ represents a substituent of the following    A₇″ group, and B_(c) is as defined above), an A₈-SO₂—B_(c)-group (A₈    represents a substituent of the following A₈ group, and B_(c) is as    defined above, provided that A₈ is not a hydrogen atom), a    R₁R₁′N—SO₂—B_(c)-group (R₁ is as defined above, R₁′ is the same as    or different from R₁, and has the same meaning as that of R₁, and    B_(c) is as defined above), a (b)-SO₂—B_(c)-group ((b) and B_(c) are    as defined above), an A₉′-B_(c)-group (A₉′ represents a substituent    of the following A₇′ group or A₈′ group, and B_(c) is as defined    above), a D₅-R₄—B_(c)-group (D₅ represents a substituent of the    following D₅ group, R₄ represents a C1-C10 alkylene group, and B_(c)    is as defined above), a M_(c)-B₃—B_(c)-group (B₃ represents a    carbonyl group, a thiocarbonyl group or a sulfonyl group, and M_(c)    and B_(c) are as defined above) or a M_(c)-B_(c)-group (M_(c) and    B_(c) are as defined above);-   (1) an A₇ group:

a C2-C10 alkenyl group optionally substituted with a halogen atom, aC2-C10 alkynyl group, a C3-C10 haloalkynyl group, a R₂—B₁—R₄-group (R₂and B₁ are as defined above, and R₄ is as defined above), a D₄-R₄-group(D₄ represents a substituent of the following D₄ group, and R₄ is asdefined above), a D₅-R₄-group (D₅ represents a substituent of thefollowing D₅ group, and R₄ is as defined above), a D₁-R₄-group {D₁represents a substituent of the following D₁ group, and R₄ is as definedabove}, a (b)-R₄-group ((b) is as defined above, and R₄ is as definedabove), a (c)-R₄-group ((c) is as defined above, and R₄ is as definedabove), a D₂-R₄-group {D₂ represents a substituent of the following D₂group, and R₄ is as defined above}, a D₃-R₄-group {D₃ represents asubstituent of the following D₃ group, and R₄ is as defined above}, anA₄-SO₂—R₄-group {A₄ represents a (b)-group ((b) is as defined above), a(c)-group ((c) is as defined above) or a R₁R₁′N-group (R₁ and R₁′ are asdefined above), and R₄ is as defined above} or an A₂-CO—R₄-group (A₂represents a substituent of the following A₂ group, and R₄ is as definedabove);

-   (2) an A₈ group: a hydrogen atom, or C1-C10 alkyl group optionally    substituted with a halogen atom;-   (3) an A₇′ group: a C3-C10 alkenyl group optionally substituted with    a halogen atom, a C3-C10 alkynyl group optionally substituted with a    halogen atom, a R₂—B₁—R₄′-group (R₂ and B₁ are as defined above, and    R₄′ represents a C2-C10 alkylene group), a D₄-R₄′ group (D₄ and R₄′    are as defined above), a D₁-R₄′-group (D₁ and R₄′ are as defined    above), a (b)-R₄′-group ((b) and R₄′ are as defined above), a    (c)-R₄′-group ((c) and R₄′ are as defined above), a D₂-R₄-group (D₂    and R₄ are as defined above), a D₃-R₄′-group (D₃ and R₄′ are as    defined above) or an A₂-CO—R₄-group (A₂ and R₄ are as defined    above);-   (4) an A₉′ group: a C1-C10 alkyl group or a C2-C10 haloalkyl group;-   (5) an A₇″ group: a C2-C10 alkenyl group, a C3-C10 alkenyl group    substituted with a halogen atom, a C3-C10 alkynyl group optionally    substituted with a halogen atom, a R₂—B₁—R₄′-group (R₂, B₁ and R₄′    are as defined above), a D₄-R₄′-group (D₄ and R₄′ are as defined    above), a D₅-R₄-group (D₅ and R₄ are as defined above), a    D₁-R₄′-group (D₁ and R₄′ are as defined above), a (b)-R₄′-group ((b)    and R₄′ are as defined above), a (c)-R₄′-group ((c) and R₄′ are as    defined above), a D₂-R₄-group (D₂ and R₄ are as defined above), a    NO₂—R₄-group (R₄ is as defined above) or an A₂-CO—R₄-group (A₂ and    R₄ are as defined above);-   (i) a D₄ group: a hydroxy group or an A₁-O-group [A₁ represents a    R₃—(CHR₀)_(m)—(B₂—B₃)_(m)′-group {R₃ represents a hydrogen atom, or    a C1-C10 alkyl group optionally substituted with a halogen atom or a    R₂—B₁-group (R₂ and B₁ are as defined above), or a C2-C10 alkenyl    group, or a C2-C10 alkynyl group, R₀ represents a hydrogen atom, a    C1-C10 alkyl group or a C2-C10haloalkyl group, m is as defined    above, B₂ represents a single bond, an oxy group, a thio group or a    —N((O)_(n)R₁′)-group (R₁′ is as defined above, and n represents 0 or    1), B₃ is as defined above, m′ represents 0 or 1 and, when B₃ is a    sulfonyl group, then m is 0, and R₃ is not a hydrogen atom}];-   (ii) a D₅ group: an O═C(R₃)-group (R₃ is as defined above), an    A₁-(O)_(n)—N═C(R₃)-group (A₁, n and R₃ are as defined above), a    R₁—B₀—CO—R₄—(O)_(n)—N═C(R₃)-group [R₁, R₄, n and R₃ are as defined    above, and B₀ represents an oxy group, a thio group or a    —N((O)_(m)R₁′)-group (R₁′ and m are as defined above)], a    D₂-R₄—(O)_(n)—N═C(R₃)-group (D₂, R₄, n and R₃ are as defined above)    or a R₁A₁N—N═C(R₃)-group (R₁, A₁ and R₃ are as defined above);-   (iii) a D₁ group: a (R)—(O)_(k))A₁N—(O)_(k)′-group (R₁ and A₁ are as    defined above, and k and k′ are the same or different, and represent    0 or 1);-   (iv) a D₂ group: a cyano group, a R₁R₁′NC(═N—(O)_(n)-A₁)-group (R₁,    R₁′, n and A₁ are as defined above), an A₁N═C—(OR₂)-group (A₁ and R₂    are as defined above) or a NH₂—CS-group;-   (v) a D₃ group: a nitro group or a R₁OSO₂-group (R₁ is as defined    above);-   (vi) an A₂ group:-   1) an A₃-B₄-group-   [A₃ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10    haloalkyl group, or a C2-C10 alkenyl group optionally substituted    with a halogen atom, or a C3-C10 alkynyl group optionally    substituted with a halogen atom, or a R_(a)—(R₄)_(m)-group (R_(a)    represents a phenyl group, a pyridyl group, a furyl group or a    thienyl group, optionally substituted with a halogen atom, a C1-C10    alkyl group, a C1-C10 alkoxy group or a nitro group, and R₄ and m    are as defined above), or a C1-C10 alkyl group substituted with a    (b)-R₄-group ((b) and R₄ are as defined above), a (c)-R₄-group ((c)    and R₄ are as defined above), a R₂—B₁—R₄-group (R₂, B₁ and R₄ are as    defined above), a D₄-R₄-group (D₄ and R₄ are as defined above), a    D₅-group (D₅ is as defined above), a D₁-R₄-group (D₁ and R₄ are as    defined above), a D₂-group (D₂ is as defined above), a D₃-R₄-group    (D₃ and R₄ are as defined above) or an A₄-SO₂—R₄-group {A₄ is as    defined above, and R₄ is as defined above},-   B₄ represents an oxy group, a thio group or a —N((O)_(m)R₁)-group    (R₁ and m are as defined above), provided that when B₄ is a thio    group, A₃ is not a hydrogen atom];-   2) a R₁—B₄—CO—R₄—B₄′-group (R₁, B₄ and R₄ are as defined above, B₄′    is the same as or different from B₄, and has the same meaning as    that of B₄, provided that when B₄ is a thio group, R₂ is not a    hydrogen atom), or a D₂-R₄—B₄-group (D₂, R₄ and B₄ are as defined    above);-   3) a R₂—SO₂—NR₁-group (R₂ is as defined above, provided that a    hydrogen atom is excluded, and R₁ is as defined above);-   4) a (b)-group ((b) is as defined above);-   5) a (c)-group ((c) is as defined above) or-   6) a R₁A₁N—NR₁′-group (R₁, A₁ and R₁′ are as defined above);-   V. M_(a)′ is the same as or different from M_(a), and has the same    meaning as that of M_(a), and r represents 0, 1, 2, 3 or 4, provided    that when an A ring is a benzene ring, in case that q is 0, then p    is 2, 3 or 4; and

the “as defined above” between a plurality of substituents indicatesthat the plurality of substituents independently represent the samemeaning as that described above and, between the plurality ofsubstituents, a selection range of selected substituents is the same,while the selected substituents may be the same or different as far asthey are selected in the range];

12. A 2H-1-benzopyran-2-one compound represented by the formula (XII):

[wherein

-   I. A represents a benzene ring or a pyridine ring;-   II. In (X_(e))_(p), X_(e) represents a hydroxy group, a halogen    atom, a C1-C10 alkyl group, a R′—S(O)l- group (R′ represents a    C1-C10 alkyl group, and l represents 0, 1 or 2), a cyano group, a    HOCO—CH═CH-group, a (R′)₂N-group (R′ is as defined above), a    R′CO—NH-group (R′ is as defined above), a nitro group or a C1-C10    alkoxy group, p represents 0, 1, 2, 3 or 4 and, when p is 2 or more,    X_(d)'s are the same or different;-   III. In (Y_(e))_(q), Y_(e) is a substituent on a carbon atom, and    represents a substituent of the following X₅ group or Y₅ group, q    represents 0, 1, 2, 3, 4 or 5, when q is 2 or more, Y_(e)'s are the    same or different and, when q is 2 or more, the adjacent two same or    different Y_(e)'s constitute a group of a Z₅ group, and may be fused    with an A ring;-   (1) a X₅ group:-   a M_(a)-group [M_(a) represents a R_(b)-group (R_(b) represents a    C1-C10 alkyl group optionally substituted with a halogen atom), a    halogen atom, a nitro group, a cyano group, a hydroxyl group, a    R_(c)—B_(a)—R_(d)-group (R_(c) represents a C1-C10 alkyl group    optionally substituted with a halogen atom, B_(a) represents an oxy    group, a thio group, a sulfinyl group or a sulfonyl group, and R_(d)    represents a single bond or a C1-C10 alkylene group), a    HOR_(d)-group (R_(d) is as defined above), a R_(e)—CO—R_(d)-group    (R_(d) represents a hydrogen atom, or a C1-C10 alkyl group    optionally substituted with a halogen atom, and R_(d) is as defined    above), a R_(e)—CO—O—R_(d)-group (R_(e) and R_(d) are as defined    above), a R_(e)O—CO—R_(d)-group (R_(e) and R_(d) are as defined    above), a HO—CO—CH═CH-group, a R_(e)R_(e)′N—R_(d)-group (R_(e) and    R_(e)′ are the same or different, R_(e) is as defined above, R_(e′)′    has the same meaning as that of R_(e), and R_(d) is as defined    above), a R_(e)—CO—NR_(e)′—R_(d)-group (R_(e), R_(e)′ and R_(d) are    as defined above), a R_(b)O—CO—N(R_(e))—R_(d)-group (R_(b), R_(e)    and R_(d) are as defined above), a R_(e)R_(e)′N—CO—R_(d)-group    (R_(e), R_(e)′ and R_(d) are as defined above), a    R_(e)R_(e)′N—CO—NR_(e)″—R_(d)-group (R_(e), R_(e)′ and R_(e)″ are    the same or different, R_(e) and R_(e)″ are as defined above, R_(e)″    has the same meaning as that of R_(e), and R_(d) is as defined    above), a R_(e)R_(e)′N—C(═NR_(e)″)—NR_(e)′″—R_(d)-group (R_(e),    R_(e)′, R_(e)″ and R_(e)′″ are the same or different, R_(e), R_(e)′    and R_(e)″ are as defined above, R_(e)′″ has the same meaning as    that of R_(e), and R_(d) is as defined above), a    R_(b)—SO₂—NR_(e)—R_(d)-group (R_(b), R_(e) and R_(d) are as defined    above), a R_(e)R_(e)′N—SO₂—R_(d)-group (R_(e), R_(e)′ and R_(d) are    as defined above), a C2-C10 alkenyl group or a C2-C10 alkynyl    group], provided that when A represents a benzene ring, then a    X_(e)-group (X_(e) is as defined above) is excluded;-   (2) a Y₅ group:-   a M_(b)-R_(d)-group [M_(b) represents a M_(c)-group {M_(c)    represents a M_(d)-R_(d)′-group {M_(d) represents a phenyl group    optionally substituted with a M_(a)-group (M_(a) is as defined    above), or a pyridyl group optionally substituted with a M_(a)-group    (M_(a) is as defined above), or a naphthyl group optionally    substituted with a M_(a)-group (M_(a) is as defined above), or

a (b)-group fin (b), G₁, G₂, G₄ and G₅ represent a methylene group whichis connected to an adjacent atom with a single bond, and may besubstituted with a methyl group, or a methine group which is connectedto an adjacent atom with a double bond, and may be substituted with amethyl group, and G₃ represents a single bond, or a double bond, or aC1-C10 alkylene group optionally substituted with a methyl group, an oxygroup, a thio group, a sulfinyl group, a sulfonyl group or a —NR₁-group{R₁ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10alkyl group substituted with a halogen atom or a R₂—B₁-group (R₂represents a C1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10alkynyl group, and B₁ represents an oxy group, a thio group, a sulfinylgroup or a sulfonyl group), or a C3-C10 alkenyl group, or a C3-C10alkynyl group}, or a C2-C10 alkenylene group optionally substituted witha methyl group, an oxy group, a thio group, a sulfinyl group, a sulfonylgroup or a —NR₁-group (R₁ is as defined above)},

a (c)-group (in (c), J₁, J₂ and J₃ are the same or different, andrepresent a methine group optionally substituted with a methyl group, ora nitrogen atom),

a (d)-group (l is 2, 3 or 4, and B_(b) represents an oxy group or a thiogroup) or

an (e)-group (l and B_(b) are as defined above), R_(d)′ is the same asor different from R_(d), and has the same meaning as that of R_(d)}}, aM_(c)-B_(a)-group (M_(c) and B_(a) are as defined above), aM_(c)-CO-group (M_(c) is as defined above), a M_(c)-CO—O-group (M_(c) isas defined above), a M_(c)O—CO-group (M_(c) is as defined above), aM_(c)R_(e)N-group (M_(c) and R_(e) are as defined above), aM_(c)-CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)O—CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO—NR_(e)′-group (M_(c), R_(e) and R_(e)′ are as definedabove), a M_(c)R_(e)N—C(═NR_(e)′)—NR_(e)-group (M_(c), R_(e), R_(e)′ andR_(e)″ are as defined above), a M_(c)-SO₂—NR_(e)-group (M_(c) and R_(e)are as defined above) or a M_(c)R_(e)N—SO₂-group (M_(c) and R_(e) are asdefined above), and R_(d) is as defined above];

-   (3) a Z₅ group:-   a —N═C(Y_(a))—Y_(a)′-group (Y_(a) represents a hydrogen atom, or a    C1-C10 alkyl group optionally substituted with a halogen atom, or a    C1-C10 alkoxy group, and Y_(a)′ represents an oxy group, or a thio    group, or an imino group optionally substituted with a C1-C10 alkyl    group), a —Y_(b)—Y_(b)′—Y_(b)″-group (Y_(b) and Y_(b)″ are the same    or different, and represent a methylene group, or an oxy group, or a    thio group, or a sulfinyl group, or an imino group optionally    substituted with a C1-C10 alkyl group, and Y_(b)′ represents a C1-C4    alkylene group optionally substituted with a halogen atom, or a    C1-C4 alkylene group optionally having an oxo group) or a    —Y_(c)—O—Y_(c)′—O-group (Y_(c) and Y_(c)′ are the same or different,    and represent a C1-C10 alkylene group), provided that when p is 0,    then Y_(e) is not fused with an A ring to form a benzo[1,3]dioxol    ring;-   IV. M_(a)′ is the same as or different from M_(a), and has the same    meaning as that of M_(a), and r represents 0, 1, 2, 3 or 4, provided    that when an A ring is a benzene ring, then q is not 0; and

the “as defined above” in the same symbol between a plurality ofsubstituents indicates that the plurality of substituents independentlyrepresent the same meaning as that described above and, between theplurality of substituents, a selection range of selected substituents isthe same, while the selected substituents may be the same or differentas far as they are selected in the range];

13. A 2H-1-benzopyran-2-one compound represented by the formula (XIII):

[wherein XII represents a hydrogen atom, or a hydroxyl group, or ahalogen atom, or a C1-C4 alkyl group optionally substituted with ahalogen atom or a C1-C4 alkoxy group, or a C2-C4 alkenyl group, or aC2-C4 alkynyl group, or a C3-C4 alkoxy group, or a R_(I)—S(O)_(l)-group(R_(I) represents a C1-C4 alkyl group, and l represents an integer of 0to 2), or a nitro group, or a cyano group, or a carboxy group, or aC1-C4 alkoxycarbonyl group, or a (R_(I))₂N-group (R_(I) is as definedabove), or a R_(I)—CO—N_(I)-group (R_(I) is as defined above), or aR_(I)O—CO—NH-group (R_(I) is as defined above), or a R_(I)NH—CO—NH-group(R_(I) is as defined above), or a (R_(I)′)₂N—CO-group (R_(I)′ representsa hydrogen atom or a C1-C4 alkyl group), or a RB-group (B represents anoxygen atom or a sulfur atom, and R represents a C1-C4 alkyl groupsubstituted with a halogen atom), k represents an integer of 1 to 4 and,when k is an integer of 2 to 4, X_(II)'s may be different, and r_(I)represents a C1-C4 alkyl group, a C2-C4 alkenyl group or a C2-C4 alkynylgroup];

14. A 2H-1-benzopyran-2-one compound represented by the formula (XIV):

[wherein X_(II)′ represents a C1-C4 alkyl group substituted with ahalogen atom or a C1-C4 alkoxy group, a C2-C4 alkenyl group, a C2-C4alkynyl group, a C3-C4 alkoxy group, a R_(I)—S(O)_(l)-group (R_(II)represents a C2-C4 alkyl group, and l represents an integer of 0 to 2),a cyano group, a carboxy group, a C1-C4 alkoxycarbonyl group, a(R_(II))₂N-group (R_(II) is as defined above), a R_(I)—CO—NH-group(R_(I) represents a C1-C4 alkyl group), a R_(I)O—CO—NH-group (R_(I) isas defined above), a R_(I)NH—CO—NH-group (R_(I) is as defined above), a(R_(I)′)₂N—CO-group (R_(I)′ represents a hydrogen atom or a C1-C4 alkylgroup) or a RB-group (B represents an oxygen atom or a sulfur atom, andR represents a C1-C4 alkyl group substituted with a halogen atom),X_(II)″ represents a hydrogen atom, a halogen atom, a C1-C4 alkyl groupor a C3-C4 alkoxy group, m represents 1 or 2 and, when m is 2, X_(II)″'smay be different];

15. A I type collagen gene transcription suppressing composition, whichcomprises a 2(1H)-pyridinone compound represented by the formula (XV):

[wherein

-   I. A represents a benzene ring or a pyridine ring;-   II. In (Y_(f))_(q), Y_(f) is a substituent on a carbon atom, and    represents a group of the following X group or Y group, q represents    0, 1, 2, 3, 4 or 5, when q is 2 or more, Y_(f)'s are the same or    different and, when q is 2 or more, the adjacent two same or    different Y_(f)'s constitutes a group of a Z group, and may be fused    with an A ring;-   (1) a X group:-   a M_(a)-group [M_(a) represents a R_(b)-group (R_(b) represents a    C1-C10 alkyl group optionally substituted with a halogen atom), a    halogen atom, a nitro group, a cyano group, a hydroxy group, a    R_(c)—B_(a)—R_(d)-group (R_(c) represents a C1-C10 alkyl group    optionally substituted with a halogen atom, B_(a) represents an oxy    group, a thio group, a sulfinyl group or a sulfonyl group, and R_(d)    represents a single bond or a C1-C10 alkylene group), a    HOR_(d)-group (R_(d) is as defined above), a R_(e)—CO—R_(d)-group    (R_(e) represents a hydrogen atom, or a C1-C10 alkyl group    optionally substituted with a halogen atom, and R_(d) is as defined    above), a R_(e)—CO—O—R_(d)-group (R_(e) and R_(d) are as defined    above), a R_(e)O—CO—R_(d)-group (R_(e) and R_(d) are as defined    above), a HO—CO—CH═CH-group, a R_(e)R_(e)′N—R_(d)-group (R_(e) and    R_(e)′ are the same or different, R_(e) is as defined above, R_(e)′    has the same meaning as that of R_(e), and R_(d) is as defined    above), a R_(e)—CO—NR_(e)′—R_(d)-group (R_(e), R_(e)′ and R_(d) are    as defined above), a R_(b)O—CO—N(R_(e))—R_(d)-group (R_(b), R_(e)    and R_(d) are as defined above), a R_(e)R_(e)′N—CO—R_(d)-group    (R_(e), R_(e)′ and R_(d) are as defined above), a    R_(e)R_(e)′N—CO—NR_(e)″—R_(d)-group (R_(e), R_(e)′ and R_(e)″ are    the same or different, R_(e) and R_(e)′ are as defined above,    R_(e)′″ has the same meaning as that of R_(e), and R_(d) is as    defined above), a R_(e)R_(e)′N—C(═NR_(e)″)—NR_(e)′″—R_(d)-group    (R_(e), R_(e)′, R_(e)″ and R_(e)′″ are the same or different, R_(e),    R_(e)′ and R_(e)″ are as defined above, R_(e)′″ has the same meaning    as that of R_(e), and R_(d) is as defined above), a    R_(b)—SO₂—NR_(e)—R_(d)-group (R_(b), R_(e) and R_(d) are as defined    above), a R_(e)R_(e)′N—SO₂—R_(d)-group (R_(e), R_(e)′ and R_(d) are    as defined above), a C2-C10 alkenyl group or a C2-C10 alkynyl    group];-   (2) a Y group:-   a M_(b)-R_(d)-group [M_(b) represents a M_(c)-group {M_(c)    represents a M_(d)-R_(d)′-group {M_(d) represents a phenyl group    optionally substituted with a M_(a)-group (M_(a) is as defined    above), or a pyridyl group optionally substituted with a M_(a)-group    (M_(a) is as defined above), or a naphthyl group optionally    substituted with a M_(a)-group (M_(a) is as defined above), or

a (b)-group {in (b), G₁, G₂, G₄ and G₅ represent a methylene group whichis connected to an adjacent atom with a single bond, and may besubstituted with a methyl group, or a methine group which is connectedto an adjacent atom with a double bond, and may be substituted with amethyl group, and G₃ represents a single bond, or a double bond, or aC1-C10 alkylene group optionally substituted with a methyl group, an oxygroup, a thio group, a sulfinyl group, a sulfonyl group or a —NR₁-group{R₁ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10alkyl group substituted with a halogen atom or a R₂—B₁-group (R₂represents a C1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10alkynyl group, and B₁ represents an oxy group, a is thio group, asulfinyl group or a sulfonyl group), or a C3-C10 alkenyl group, or aC3-C10 alkynyl group}, or a C2-C10 alkenylene group optionallysubstituted with a methyl group, an oxy group, a thio group, a sulfinylgroup, a sulfonyl group or a —NR₁-group (R₁ is as defined above)},

a (c)-group (in (c), J₁, J₂ and J₃ are the same or different, andrepresent a methine group optionally substituted with a methyl group, ora nitrogen atom),

a (d)-group (l is 2, 3 or 4, and B_(b) represents an oxy group or a thiogroup) or

an (e)-group (l and B_(b) are as defined above), R_(d)′ is the same asor different from R_(d), and has the same meaning as that of R_(d)}}, aM_(c)-B_(a)-group (M_(c) and B_(a) are as defined above), aM_(c)-CO-group (M_(c) is as defined above), a M_(c)-CO—O-group (M_(c) isas defined above), a M_(c)O—CO-group (M_(c) is as defined above), aM_(c)R_(e)N-group (M_(c) and R_(e) are as defined above), aM_(c)-CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)O—CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO—NR_(e)′-group (M_(c), R_(e) and R_(e)′ are as definedabove), a M_(c)R_(e)N—C(═NR_(e)′)—NR_(e)″-group (M_(c), R_(e), R_(e)′and R_(e)″ are as defined above), a M_(c)-SO₂—NR_(e)-group (M_(c) andR_(e) are as defined above) or a M_(c)R_(e)N—SO₂-group (M_(c) and R_(e)are as defined above), and R_(d) is as defined above];

-   (3) a Z group: a —N═C(Y_(a))—Y_(a)′-group (Y_(a) represents a    hydrogen atom, or a C1-C10 alkyl group optionally substituted with a    halogen atom, or a C1-C10 alkoxy group, and Y_(a)′ represents an    imino group optionally substituted with an oxy group, or a thio    group, or a C1-C10 alkyl group), a —Y_(b)—Y_(b)′—Y_(b)″-group (Y_(b)    and Y_(b)″ are the same or different, and represent a methylene    group, or an oxy group, or a thio group, or a sulfinyl group, or an    imino group optionally substituted with a C1-C10 alkyl group, and    Y_(b)′ represents a C1-C4alkylene group optionally substituted with    a halogen atom, or a C1-C4alkylene group optionally having an oxo    group), or a —Y_(c)—O—Y_(c)′—O-group (Y_(c) and Y_(c)′ are the same    or different, and represent a C1-C10 alkylene group);-   III. Q_(A) represents a hydroxyl group, a (b)-group ((b) is as    defined above), an A₉-B₆—B_(c)-group [A₉ represents a substituent of    the following A₇ group or A₈ group, B₆ represents a carbonyl group    or a thiocarbonyl group, and B_(c) represents an oxy group or a    —N((O)_(m)R₁)-group (m represents 0 or 1, and R₁ is as defined    above), provided that when A₉ is a hydrogen atom, then B_(c) is not    a sulfonyl group], an A₇″-SO₂—B_(c)-group (A₇″ represents a    substituent of the following A₇″ group, and B_(c) is as defined    above), an A₈-SO₂—B_(c)-group (A₈ represents a substituent of the    following A₈ group, and B_(c) is as defined above, provided that A₈    is not a hydrogen atom), a R₁R₁′N—SO₂—B_(c) group (R₁ is as defined    above, R₁′ is the same as or different of R₁, and has the same    meaning of R₁, and B_(c) is as defined above), a (b)-SO₂—B_(c)-group    ((b) and B_(c) are as defined above), an A₉′-B_(c)-group (A₉′    represents a substituent of the following A₇′ group or a A₈′ group,    and B_(c) is as defined above), a D₅-R₄—B_(c)-group (D₅ represents a    substituent of the following D₅ group, R₄ represents a C1-C10    alkylene group, and B_(c) is as defined above), a    M_(c)-B₃—B_(c)-group (B₃ represents a carbonyl group, a thiocarbonyl    group or a sulfonyl group, and M_(c) and B_(c) are as defined above)    or a M_(c)-B_(c)-group (M_(c) and B_(c) are as defined above);-   (1) an A₇ group:-   a C2-C10 alkenyl group optionally substituted with a halogen atom, a    C2-C10 alkynyl group, a C3-C10 haloalkynyl group, a R₂—B₁—R₄-group    (R₂ and B₁ are as defined above, and R₄ is as defined above), a    D₄-R₄-group (D₄ represents a substituent of the following D₄ group,    and R₄ is as defined above), a D₅-R₄-group (D₅ represents a    substituent of the following D₅ group, and R₄ is as defined above),    a D₁-R₄-group {D₁ represents a substituent of the following D₁    group, and R₄ is as defined above}, a (b)-R₄-group ((b) is as    defined above, and R₄ is as defined above), a (c)-R₄-group ((c) is    as defined above, and R₄ is as defined above), a D₂-R₄-group {D₂    represents a substituent of the following D₂ group, and R₄ is as    defined above}, a D₃-R₄-group {D₃ represents a substituent of the    following D₃ group, and R₄ is as defined above}, an A₄-SO₂—R₄-group    {A₄ represents a (b)-group ((b) is as defined above), a (c)-group    ((c) is as defined above) or a R₁R₁′N-group (R₁ and R₁′ are as    defined above), and R₄ is as defined above} or an A₂-CO—R₄-group (A₂    represents a substituent of the following A₂ group, and R₄ is as    defined above);-   (2) an A₈ group: a hydrogen atom, or a C1-C10 alkyl group optionally    substituted with a halogen atom;-   (3) an A₇′ group: a C3-C10 alkenyl group optionally substituted with    a halogen atom, a C3-C10 alkynyl group optionally substituted with a    halogen atom, a R₂—B₁—R₄′-group (R₂ and B₁ are as defined above, and    R₄′ represents a C2-C10 alkylene group), a D₄-R₄′-group (D₄ and R₄′    are as defined above), a D₁-R₄′-group (D₁ and R₄′ are as defined    above), a (b)-R₄′-group ((b) and R₄′ are as defined above), a    (c)-R₄′-group ((c) and R₄′ are as defined above), a D₂-R₄-group (D₂    and R₄ are as defined above), a D₃-R₄′-group (D₃ and R₄′ are as    defined above) or an A₂-CO—R₄-group (A₂ and R₄ are as defined    above);-   (4) an A₈′ group: a C1-C10 alkyl group or a 2-C10 haloalkyl group;-   (5) an A₇″ group: a C2-C10 alkenyl group, a C3-C10 alkenyl group    substituted with a halogen atom, a C3-C10 alkynyl group optionally    substituted with a halogen atom, a R₂—B₁—R₄′-group (R₂, B₁ and R₄′    are as defined above), a D₄-R₄′-group (D₄ and R₄′ are as defined    above), a D₅-R₄-group (D₅ and R₄ are as defined above), a    D₁-R₄′-group (D₁ and R₄′ are as defined above), a (b)-R₄′-group ((b)    and R₄′ are as defined above), a (c)-R₄′-group ((c) and R₄′ are as    defined above), a D₂-R₄-group (D₂ and R₄ are as defined above), a    NO₂—R₄-group (R₄ is as defined above) or an A₂-CO—R₄-group (A₂ and    R₄ are as defined above);-   (i) a D₄ group: a hydroxy group or an A₁-O-group [A₁ represents a    R₃—(CHR₀)_(m)—(B₂—B₃)_(m′)-group {R₃ represents a hydrogen atom, or    a C1-C10 alkyl group optionally substituted with a halogen atom or a    R₂—B₁-group (R₂ and B₁ are as defined above), or a C2-C10 alkenyl    group, or a C2-C10 alkynyl group, R₀ represents a hydrogen atom, a    C1-C10 alkyl group or a C2-C10 haloalkyl group, m is as defined    above, B₂ represents a single bond, an oxy group, a thio group or a    —N((O)_(n)R₁′)-group (R₁′ is as defined above, and n represents 0 or    1), B₃ is as defined above, m′ represents 0 or 1 and, when B₃ is a    sulfonyl group, then m is 0, and R₃ is not a hydrogen atom}];-   (ii) a D₅ group: an O═C(R₃)-group (R₃ is as defined above), an    A₁-(O)_(n)—N═C(R₃)-group (A₁, n and R₃ are as defined above), a    R₁—B₀—CO—R₄—(O)_(n)—N═C(R₃)-group [R₁, R₄, n and R₃ are as defined    above, and B₀ represents an oxy group, a thio group or a    —N((O)_(m)R₁′)-group (R₁′ and m are as defined above)], a D₂-R₄—    (O)_(n)—N═C(R₃)-group (D₂, R₄, n and R₃ are as defined above) or a    R₁A₁N—N═C(R₃)-group (R₁, A₁ and R₃ are as defined above);-   (iii) a D₁ group: a (R₁—(O)_(k)-)A₁N—(O)_(k)′-group (R₁ and A₁ are    as defined above, and k and k′ are the same or different, and    represent 0 or 1);-   (iv) a D₂ group: a cyano group, a R₁R₁′NC(═N—(O)_(n)-A₁)-group (R₁,    R₁′, n and A₁ are as defined above), an A₁N═C(—OR₂)-group (A₁ and R₂    are as defined above) or a NH₂—CS-group;-   (v) a D₃ group: a nitro group or a R₁OSO₂-group (R₁ is as defined    above);-   (vi) an A₂ group:-   1) an A₃-B₄-group-   [A₃ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10    haloalkyl group, or a C2-C10 alkenyl group optionally substituted    with a halogen atom, or a C3-C10 alkynyl group optionally    substituted with a halogen atom, or a R_(a)—(R₄)_(m)-group (R_(a)    represents a phenyl group, a pyridyl group, a furyl group or a    thienyl group, optionally substituted with a halogen atom, a C1-C10    alkyl group, a C1-C10 alkoxy group or a nitro group, and R₄ and m    are as defined above), or a C1-C10 alkyl group substituted with a    (b)-R₄-group ((b) and R₄ are as defined above), a (c)-R₄-group ((c)    and R₄ are as defined above)], a R₂—B₁—R₄-group (R₂, B₁ and R₄ are    as defined above), a D₄-R₄-group (D₄ and R₄ are as defined above), a    D₅-group (D₅ is as defined above), a D₁-R₄-group (D₁ and R₄ are as    defined above), a D₂-group (D₂ is as defined above), a D₃-R₄-group    (D₃ and R₄ are as defined above) or an A₄-SO₂—R₄-group {A₄ is as    defined above, and R₄ is as defined above},

B₄ represents an oxy group, a thio group, or a —N((O)_(m)R₁)-group (R₁and m are as defined above), provided that when B₄ is a thio group, thenA₃ is not a hydrogen atom];

-   2) a R₁—B₄—CO—R₄—B₄′-group (R₁, B₄ and R₄ are as defined above, B₄′    is the same as or different from R₄, and has the same meaning as    that of B₄, provided that when R₄ is a thio group, then R₂ is not a    hydrogen atom) or a D₂-R₄—B₄-group (D₂, R₄ and B₄ are as defined    above);-   3) a R₂—SO₂—NR₁-group (R₂ is as defined above, provided that a    hydrogen atom is excluded, and R₁ is as defined above);-   4) a (b)-group ((b) is as defined above);-   5) a (c)-group ((c) is as defined above) or-   6) a R₁A₁N—NR₁′-group (R₁, A₁ and R₁′ are as defined above);-   IV. T_(A) represents a hydrogen atom, an A₉′-group (A₉′ is as    defined above), a D₅-R₄-group (D₅ and R₄ are as defined above) or a    M_(c)-group (M_(c) is as defined above);-   V. K_(a) represents a hydrogen atom, a halogen atom or a C1-C10    alkyl group, L_(a) represents a hydrogen atom, a C1-C10 alkyl group    or a M_(b)-group (M_(b) is as defined above) or a K_(a) and L_(a)    may form a C1-C10 alkylene group; and

the “as defined above” in the same symbol between a plurality ofsubstituents indicates that the plurality of substituents independentlyrepresent the same meaning as that described above and, between theplurality of substituents, a selection range of selected substituents isthe same, while the selected substituents may be the same or differentas far as they are selected in the range]; and an inert carrier;

16. A 2(1H)-pyridinone compound represented by the formula (XVI):

[wherein

-   I. A represents a benzene ring or a pyridine ring;-   II. In (X_(g))_(p), X_(g) represents a hydroxyl group, a halogen    atom, a (R′)₂N-group (R′ represents a C1-C10 alkyl group), a nitro    group or a C1-C10 alkoxy group, p represents 0, 1, 2, 3 or 4 and,    when p is 2 or more, X_(g)'s are the same or different;-   III. In (Y_(g))_(q), Y_(g) is a substituent on a carbon atom, and    represents a group of the following X₆ group or Y₆ group, q    represents 0, 1, 2, 3, 4 or 5, when q is 2 or more, Y_(g)'s are the    same or different and, when q is 2 or more, the adjacent two same or    different Y_(g)'s constitutes a group of a Z₆ group, and may be    fused with an A ring;-   (1) a X₆ group:-   a M_(a)-group [M_(a) represents a R_(b)-group (R_(b) represents a    C1-C10 alkyl group optionally substituted with a halogen atom), a    halogen atom, a nitro group, a cyano group, a hydroxyl group, a    R_(c)—B_(a)—R_(d)-group (R_(c) represents a C1-C10 alkyl group    optionally substituted with a halogen atom, B_(a) represents an oxy    group, a thio group, a sulfinyl group or a sulfonyl group, and R_(d)    represents a single bond or a C1-C10 alkylene group), a    HOR_(d)-group (R_(d) is as defined above), a R_(e)—CO—R_(d)-group    (R_(e) represents a hydrogen atom, or a C1-C10 alkyl group    optionally substituted with a halogen atom, and R_(d) is as defined    above), a R_(e)—CO—O—R_(d)-group (R_(e) and R_(d) are as defined    above), a R_(e)O—CO—R_(d)-group (R_(e) and R_(d) are as defined    above), a HO—CO—CH═CH-group, a R_(e)R_(e)′N—R_(d)-group (R_(e) and    R_(e)′ are the same or different, R_(e) is as defined above, R_(e)′    has the same meaning as that of R_(e), and R_(d) is as defined    above), a R_(e)—CO—NR_(e)′—R_(d)-group (R_(e), R_(e)′ and R_(d) are    as defined above), a R_(b)O—CO—N(R_(e))—R_(d)-group (R_(b), R_(e)    and R_(d) are as defined above), a R_(e)R_(e)′N—CO—R_(d)-group    (R_(e), R_(e)′ and R_(d) are as defined above), a    R_(e)R_(e)′N—CO—NR_(e)″—R_(d)-group (R_(e), R_(e)′ and R_(e)″ are    the same or different, R_(e) and R_(e)′ are as defined above, R_(e)″    has the same meaning as that of a R_(e), and R_(d) is as defined    above), a R_(e)R_(e)′N—C(═NR_(e)″)—NR_(e)′″—R_(d)-group (R_(e),    R_(e)′, R_(e)″ and R′″ are the same or different, R_(e), R_(e)′ and    R_(e)″ are as defined above, R_(e)′″ has the same meaning as that of    R_(e), and R_(d) is as defined above), a    R_(b)—SO₂—NR_(e)—R_(d)-group (R_(b), R_(e) and R_(d) are as defined    above), a R_(e)R_(e)′N—SO₂—R_(d)-group (R_(e), R_(e)′ and R_(d) are    as defined above), a C2-C10 alkenyl group or a C2-C10 alkynyl    group], provided that when A represents a benzene ring, then a    X_(g)-group (X_(g) is as defined above) is excluded;-   (2) a Y₆ group:-   a M_(b)-R_(d)-group [M_(b) represents a M_(c)-group {M_(c)    represents a M_(d)-R_(d)′-group {M_(d) represents a phenyl group    optionally substituted with a M_(a)-group (M_(a) is as defined    above), or a pyridyl group optionally substituted with a M_(a)-group    (M_(a) is as defined above), or a naphthyl group optionally    substituted with a M_(a)-group (M_(a) is as defined above), or

a (b)-group {in (b), G₁, G₂, G₄ and G₅ represent a methylene group whichis connected to an adjacent atom with a single bond, and may besubstituted with a methyl group, or a methine group which is connectedto an adjacent atom with a double bond and may be substituted with amethyl group, and G₃ represents a single bond, or a double bond, or aC1-C10 alkylene group optionally substituted with a methyl group, an oxygroup, a thio group, a sulfinyl group, a sulfonyl group or a —NR₁-group{R₁ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10alkyl group substituted with a halogen atom or a R₂—B₁-group (R₂represents a C1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10alkynyl group, and B₁ represents an oxy group, a thio group, a sulfinylgroup or a sulfonyl group), or a C3-C10 alkenyl group, or a C3-C10alkynyl group}, or a C2-C10 alkenylene group optionally substituted witha methyl group, an oxy group, a thio group, a sulfinyl group, a sulfonylgroup or a —NR₁-group (R₁ is as defined above)},

a (c)-group (in (c), J₁, J₂ and J₃ are the same or different, andrepresent a methine group optionally substituted with a methyl group, ora nitrogen atom),

a (d)-group (l is 2, 3 or 4, and B_(b) represents an oxy group or a thiogroup)or

an (e)-group (l and B_(b) are as defined above), R_(d)′ is the same asor different from R_(d), and has the same meaning as that of R_(d)}}, aM_(c)-B_(a)-group (M_(c) and B_(a) are as defined above), aM_(c)-CO-group (M_(c) is as defined above), a M_(c)-CO—O-group (M_(c) isas defined above), a M_(c)O—CO-group (M_(c) is as defined above), aM_(c)R_(e)N-group (M_(c) and R_(e) are as defined above), aM_(c)-CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)O—CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO—NR_(e)′-group (M_(c), R_(e) and R_(e)′ are as definedabove), a M_(c)R_(e)N—C(═NR_(e)′)—NR_(e)″-group (M_(c), R_(e), R_(e)′and R_(e)″ are as defined above), a M_(c)-SO₂—NR_(e)-group (M_(c) andR_(e) are as defined above) or a M_(c)R_(e)N—SO₂-group (M_(c) and R_(e)are as defined above), and R_(d) is as defined above];

-   (3) a Z₆ group:

a —N═C(Y_(a))—Y_(a)′-group (Y_(a) represents a hydrogen atom, or aC1-C10 alkyl group optionally substituted with a halogen atom, or aC1-C10 alkoxy group, and Y_(a)′ represents an oxy group, or a thiogroup, or an imino group optionally substituted with a C1-C10 alkylgroup), a —Y_(b)—Y_(b)′—Y_(b)″-group (Y_(b) and Y_(b)″ are the same ordifferent, a methylene group, or an oxy group, or a thio group, or asulfinyl group, or an imino group optionally substituted with a C1-C10alkyl group, and Y_(b)′ represents a C1-C4alkylene group optionallysubstituted with a halogen atom, or a C1-C4 alkylene group optionallyhaving an oxo group) or a —Y_(c)—O—Y_(c)′—O-group (Y_(c) and Y_(c)′ arethe same or different, and represent a C1-C10 alkylene group);

-   IV. Q_(A) represents a hydroxyl group, a (b)-group ((b) is as    defined above), an A₉-B₆—B_(c)-group [A₉ represents a substituent of    the following A₇ group or A₈ group, B₆ represents a carbonyl group    or a thiocarbonyl group, and B_(c) represents an oxy group or a    —N((O)_(m)R₁)-group (m represents 0 or 1, and R₁ is as defined    above), provided that when A₉ is a hydrogen atom, then B_(c) is not    a sulfonyl group], an A₇″-SO₂—B_(c)-group (A₇″ represents a    substituent of the following A₇″ group, and B_(c) is as defined    above), an A₈-SO₂—B_(c)-group (A₈ represents a substituent of the    following A₈ group, B₁ is as defined above, provided that A₈ is not    a hydrogen atom), a R₁R₁′N—SO₂—B_(c)-group (R₁ is as defined above,    R₁′ is the same as or different from R₁, and has the same meaning as    that of R₁, and B_(c) is as defined above), a (b)-SO₂—B_(c)-group    ((b) and B_(c) are as defined above), an A₉′-B_(c)-group (A₉′    represents a substituent of the following A₇′ group or A₈′ group,    and B_(c) is as defined above), a D₅-R₄—B_(c)-group (D₅ represents a    substituent of the following D₅ group, R₄ represents a C1-C10    alkylene group, and B_(c) is as defined above), a    M_(c)-B₃—B_(c)-group (B₃ represents a carbonyl group, a thiocarbonyl    group or a sulfonyl group, and M_(c) and B_(c) are as defined    above), or a M_(c)-B_(c)-group (M_(c) and B_(c) are as defined    above);-   (1) an A₇ group:-   a C2-C10 alkenyl group optionally substituted with a halogen atom, a    C2-C10 alkynyl group, a C3-C10 haloalkynyl group, a R₂—B₁—R₄-group    (R₂ and B₁ are as defined above, and R₄ is as defined above), a    D₄-R₄-group (D₄ represents a substituent of the following D₄ group,    and R₄ is as defined above), a D₅-R₄-group (D₅ represents a    substituent of the following D₅ group, and R₄ is as defined above),    a D₁-R₄-group {D₁ represents a substituent of the following D₁    group, and R₄ is as defined above}, a (b)-R₄-group ((b) is as    defined above, and R₄ is as defined above), a (c)-R₄-group ((c) is    as defined above, and R₄ is as defined above), a D₂-R₄-group (D₂    represents a substituent of the following D₂ group, and R₄ is as    defined above), a D₃-R₄-group {D₃ represents a substituent of the    following D₃ group, and R₄ is as defined above}, an A₄-SO₂—R₄-group    {A₄ represents a -(b)-group ((b) is as defined above), a (c)-group    ((c) is as defined above) or a R₁R₁′N-group (R₁ and R₁′ are as    defined above), and R₄ is as defined above} or an A₂-CO—R₄ group (A₂    represents a substituent of the following A₂ group, and R₄ is as    defined above);-   (2) an A₈ group: a hydrogen atom, or a C1-C10 alkyl group optionally    substituted with a halogen atom;-   (3) an A₇′ group: a C3-C10 alkenyl group optionally substituted with    a halogen atom, a C3-C10 alkynyl group optionally substituted with a    halogen atom, a R₂—B₁—R₄′-group (R₂ and B₁ are as defined above, and    R₄′ represents a C2-C10 alkylene group), a D₄-R₄′-group (D₄ and R₄′    are as defined above), a D₁-R₄′-group (D₁ and R₄′ are as defined    above), a (b)-R₄′-group ((b) and R₄′ are as defined above), a    (c)-R₄′-group ((c) and R₄′ are as defined above), a D₂-R₄-group (D₂    and R₄ are as defined above), a D₃-R₄′-group (D₃ and R₄′ are as    defined above), and an A₂-CO—R₄-group (A₂ and R₄ are as defined    above);-   (4) an A₈′ group: a C1-C10 alkyl group or a C2-C10 haloalkyl group;-   (5) an A₇″ group: a C2-C10 alkenyl group, a C3-C10 alkenyl group    substituted with a halogen atom, a C3-C10 alkynyl group optionally    substituted with a halogen atom, a R₂—B₁—R₄′-group (R₂, B₁ and R₄′    are as defined above), a D₄-R₄′-group (D₄ and R₄′ are as defined    above), a D₅-R₄-group (D₅ and R₄ are as defined above), a    D₁-R₄′-group (D₁ and R₄′ are as defined above), a (b)-R₄′-group ((b)    and R₄′ are as defined above), a (c)-R₄′-group ((c) and R₄′ are as    defined above), a D₂-R₄-group (D₂ and R₄ are as defined above), a    NO₂—R₄-group (R₄ is as defined above) or an A₂-CO—R₄-group (A₂ and    R₄ are as defined above);-   (i) a D₄ group: a hydroxyl group or an A₁-O-group [A₁ represents a    R₃—(CHR₀)_(m)—(B₂—B₃)_(m′)-group {R₃ represents a hydrogen atom, or    a C1-10 alkyl group optionally substituted with a halogen atom or a    R₂—B₁-group (R₂ and B₁ are as defined above), or a C1-C10 alkenyl    group, or a C2-C10 alkynyl group, R₀ represents a hydrogen atom, a    C1-C10 alkyl group or a C2-C10 haloalkyl group, m is as defined    above, B₂ represents a single bond, an oxy group, a thio group or a    —N((O)_(n)R₁)— group (R₁′ is as defined above, and n represents 0 or    1), B₃ is as defined above, m′ represents 0 or 1 and, when B₃ is a    sulfonyl group, m is 0, and R₃ is not a hydrogen atom}];-   (ii) a D₅ group: an O═C(R₃)-group (R₃ is as defined above), an    A₁-(O)_(n)—N═C(R₃)-group (A₁, n and R₃ are as defined above), a    R₁—B₀—CO—R₄—(O)_(n)—N═C(R₃)-group [R₁, R₄, n and R₃ are as defined    above, and B₀ represents an oxy group, a thio group or a    —N((O)_(m)R₁′)-group (R₁′ and m are as defined above)], a    D₂-R₄—(O)_(n)—N═C(R₃)-group (D₂, R₄, n and R₃ are as defined above)    or a R₁A₁N—N═C(R₃)-group (R₁, A₁ and R₃ are as defined above);-   (iii) a D₁ group: a (R₁—(O)_(k)-)A₁N—(O)_(k)′-group (R₁ and A₁ are    as defined above, and k and k′ are the same or different, and    represent 0 or 1);-   (iv) a D₂ group: a cyano group, a R₁R₁′NC(═N—(O)_(n)-A₁)-group (R₁,    R₁′, n and A₁ are as defined above), an A₁N═C(—OR₂)-group (A₁ and R₂    are as defined above) or a NH₂—CS-group;-   (v) a D₃ group: a nitro group or a R₁OSO₂-group (R₁ is as defined    above);-   (vi) an A₂ group:-   1) an A₃-B₄-group-   [A₃ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10    haloalkyl group, or a C2-C10 alkenyl group optionally substituted    with a halogen atom, or a C3-C10 alkynyl group optionally    substituted with a halogen atom, or a R_(a)—(R₄)_(m)-group (R_(a)    represents a phenyl group, a pyridyl group, a furyl group or a    thienyl group, optionally substituted with a halogen atom, a C1-C10    alkyl group a C1-C10 alkoxy group or a nitro group, and R₄ and m are    as defined above), or a C1-C10 alkyl group substituted with a    (b)-R₄-group ((b) and R₄ are as defined above), a (c)-R₄-group ((c)    and R₄ are as defined above), a R₂—B₁—R₄-group (R₂, B₁ and R₄ are as    defined above), a D₄-R₄-group (D₄ and R₄ are as defined above), a    D₅-group (D₅ is as defined above), a D₁-R₄-group (D₁ and R₄ are as    defined above), a D₂-group (D₂ is as defined above), a D₃-R₄-group    (D₃ and R₄ are as defined above) or an A₄-SO₂—R₄-group {A₄ is as    defined above, and R₄ is as defined above}, B₄ represents an oxy    group, a thio group or a —N((O)_(m)R₁)-group (R₁ and m are as    defined above), provided that when B₄ is a thio group, then A₃ is    not a hydrogen atom];-   2) a R₁—B₄—CO—R₄—B₄′-group (R₁, B₄ and R₄ are as defined above, B₄′    is the same as or different from B₄, and has the same meaning as    that of B₄, provided that when B₄ is a thio group, then R₂ is not a    hydrogen atom) or a D₂-R₄—B₄-group (D₂, R₄ and B₄ are as defined    above);-   3) a R₂—SO₂—NR₁-group (R₂ is as defined above, provided that a    hydrogen atom is excluded, and R₁ is as defined above);-   4) a (b)-group ((b) is as defined above);-   5) a (c)-group ((c) is as defined above) or-   6) a R₁A₁N—NR₁′-group (R₁, A₁ and R₁′ are as defined above);-   V. T_(A) represents a hydrogen atom, an A₉′-group (A₉′ is as defined    above), a D₅-R₄-group (D₅ and R₄ are as defined above) or a    M_(c)-group (m_(c) is as defined above);-   VI. K_(a) represents a hydrogen atom, a halogen atom or a C1-C10    alkyl group, L_(a) represents a hydrogen atom, a C1-C10 alkyl group    or a M_(b)-group (M_(b) is as defined above), or K_(a) and L_(a) may    form a C1-C10 alkylene group, provided that when an A ring is a    benzene ring, then q is not 0; and

the “as defined above” in the same symbol between a plurality ofsubstituents indicates that the plurality of substituents independentlyrepresent the same meaning as that described above and, between theplurality of substituents, a selection range of selected substituents isthe same, while the selected substituents may be the same or differentas far as they are selected in the range];

17. A I type collagen gene transcription suppressing composition, whichcomprises a 2(1H)-pyridinone compound represented by the formula (XVII):

[wherein XIII represents a hydrogen atom, or a hydroxy group, or ahalogen atom, or a C1-C4 alkyl group optionally substituted with ahalogen atom or a C1-C4 alkoxy group, or a C2-C4 alkenyl group, or aC2-C4 alkynyl group, or a C1-C4 alkoxy group, or a R₁—S(O)_(l)-group (R₁represents a C1-C4 alkyl group, and l represents an integer of 0 to 2),or a nitro group, or a cyano group, or a carboxy group, or a C1-C4alkoxycarbonyl group, or a (R_(I))₂N-group (R_(I) is as defined above),or a R_(I)—CO—NH-group (R_(I) is as defined above), or aR_(I)O—CO—NH-group (R_(I) is as defined above), or a R_(I)NH—CO—NH-group(R_(I) is as defined above), or a (R_(I)′)₂N—CO-group (R_(I)′ representsa hydrogen atom or a C1-C4 alkyl group) or a RB-group (B represents anoxygen atom or a sulfur atom, and R represents a C1-C4 alkyl groupsubstituted with a halogen atom), K represents an integer of 1 to 4,when k is an integer of 2 to 4, X_(III)'s may be different, r_(II) andr_(II′) are the same or different, and represent a hydrogen atom or aC1-C4 alkyl group];

-   and an inert carrier;

18. A 2(1H)-pyridinone compound represented by the formula (XVIII):

[wherein X_(III)′ represents a C2-C4 alkyl group, or a C1-C4 alkyl groupsubstituted with a halogen atom or a C1-C4 alkoxy group, or a C2-C4alkenyl group, or a C2-C4 alkynyl group, or a C2-C4 alkoxy group, or aR_(I)—S(O)_(l)-group (R_(I) represents a C1-C4 alkyl group, and lrepresents an integer of 0 to 2), or a cyano group, or a carboxy group,or a C1-C4 alkoxycarbonyl group, a (R_(II))₂N-group (R_(II) represents aC2-C4 alkyl group), or a R_(I)—CO—NH-group (R_(I) is as defined above),or a R_(I)O—CO—NH-group (R_(I) is as defined above), or aR_(I)NH—CO—NH-group (R_(I) is as defined above), or a(R_(I)′)₂N—CO-group (R_(I)′ represents a hydrogen atom or a C1-C4 alkylgroup), or a RB-group (B represents an oxygen atom or a sulfur atom, andR represents a C1-C4 alkyl group substituted with a halogen atom),X_(III)″ represents a hydrogen atom, a halogen atom, a C1-C4 alkylgroup, or a C1-C4 alkoxy group, m represents 1 or 2, when m is 2,X_(III)″'s may be different, and r_(II) and r_(II′) are the same ordifferent, and represent a hydrogen atom or a C1-C4alkyl group];

19. A I type collagen gene transcription suppressing composition, whichcomprises a 2(1H)-quinolinone compound represented by the formula (XIX):

[wherein

-   I. A represents a benzene ring or a pyridine ring;-   II. In (Y_(f))_(q), Y_(f) is a substituent on a carbon atom, and    represents a group of the following X group or Y group, q represents    0, 1, 2, 3, 4 or 5, when q is 2 or more, Y_(f)'s are the same or    different and, when q is 2 or more, the adjacent two same or    different Y_(f)'s constitute a group of a Z group, and may be fused    with an A ring;-   (1) a X group:-   a M_(a)-group [M_(a) represents a R_(b)-group (R_(b) represents a    C1-C10 alkyl group optionally substituted with a halogen atom), a    halogen atom, a nitro group, a cyano group, a hydroxyl group, a    R_(c)—B_(a)—R_(d)-group (R_(c) represents a C1-C10 alkyl group    optionally substituted with a halogen atom, B_(a) represents an oxy    group, a thio group, a sulfinyl group or a sulfonyl group, and R_(d)    represents a single bond or a C1-C10 alkylene group), a    HOR_(d)-group (R_(d) is as defined above), a R_(e)—CO—R_(d)-group    (R_(e) represents a hydrogen atom, or a C1-C10 alkyl group    optionally substituted with a halogen atom, and R_(d) is as defined    above), a R_(e)—CO—O—R_(d)-group (R_(e) and R_(d) are as defined    above), a R_(e)O—CO—R_(d)-group (R_(e) and R_(d) are as defined    above), a HO—CO—CH═CH-group, a R_(e)R_(e)′N—R_(d)-group (R_(e) and    R_(e)′ are the same or different, R_(e) is as defined above, R_(e)′    has the same meaning as that of R_(e), and R_(d) is as defined    above), a R_(e)—CO—NR_(e)′ —R_(d)-group (R_(e), R_(e)′ and R_(d) are    as defined above), a R_(b)O—CO—N(R_(e))—R_(d)-group (R_(b), R_(e)    and R_(d) are as defined above), a R_(e)R_(e)′N—CO—R_(d)-group    (R_(e), R_(e)′ and R_(d) are as defined above), a    R_(e)R_(e)′N—CO—NR_(e)″—R_(d)-group (R_(e), R_(e)′ and R_(e)″ are    the same or different, R_(e) and R_(e)′ are as defined above, R_(e)″    has the same meaning as that of R_(e), and R_(d) is as defined    above), a R_(e)R_(e)′N—C(═NR_(e)″)—NR_(e)′″—R_(d)-group (R_(e),    R_(e)′, R_(e)″ and R_(e)″ are the same or different, R_(e), R_(e)′    and R_(e)″ are as defined above, R_(e)′″ has the same meaning as    that of R_(e), and R_(d) is as defined above), a    R_(b)—SO₂—NR_(e)—R_(d)-group (R_(b), R_(e) and R_(d) are as defined    above), a R_(e)R_(e)′N—SO₂—R_(d)-group (R_(e), R_(e)′ and R_(d) are    as defined above), a C2-C10 alkenyl group or a C2-C10 alkynyl    group];-   (2) a Y group:-   a M_(b)-R_(d)-group [M_(b) represents a M_(c)-group {M_(c)    represents a M_(d)-R_(d)′-group {M_(d) represents a phenyl group    optionally substituted with a M_(a)-group (M_(a) is as defined    above), or a pyridyl group optionally substituted with a M_(a)-group    (M_(a) is as defined above), or a naphthyl group optionally    substituted with a M_(a)-group (M_(a) is as defined above), or

a (b)-group {in (b), G₁, G₂, G₄ and G₅ represent a methylene group whichis connected to an adjacent atom with a single bond, and may besubstituted with a methyl group, or a methine group which is connectedto an adjacent atom with a double bond, and may be substituted with amethyl group, and G₃ represents a single bond, or a double bond, or aC1-C10 alkylene group optionally substituted with a methyl group, an oxygroup, a thio group, a sulfinyl group, a sulfonyl group or a —NR₁-group{R₁ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10alkyl group substituted with a halogen atom or a R₂—B₁-group (R₂represents a C1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10alkynyl group, and B₁ represents an oxy group, a thio group, a sulfinylgroup or a sulfonyl group), or a C3-C10 alkenyl group, or a C3-C10alkynyl group}, or a C2-C10 alkenylene group optionally substituted witha methyl group, an oxy group, a thio group, a sulfinyl group, a sulfonylgroup or a —NR₁-group (R₁ is as defined above)},

a (c)-group (in (c), J₁, J₂ and J₃ are the same or different, andrepresent a methine group optionally substituted with a methyl group, ora nitrogen atom),

a (d)-group (l is 2, 3 or 4, and B_(b) represents an oxy group or a thiogroup)or

an (e)-group (l and B_(b) are as defined above), R_(d)′ is the same asor different from R_(d), and has the same meaning as that of R_(d)}}, aM_(c)-B_(a)-group (M_(c) and B_(a) are as defined above), aM_(c)-CO-group (M_(c) is as defined above), a M_(c)-CO—O-group (M_(c) isas defined above), a M_(c)O—CO-group (M_(c) is as defined above), aM_(c)R_(e)N-group (M_(c) and R_(e) are as defined above), aM_(c)-CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)O—CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO—NR_(e)′-group (M_(c), R_(e) and R_(e)′ are as definedabove), a M_(c)R_(e)N—C(═NR_(e)′)—NR_(e)″-group (M_(c), R_(e), R_(e)′and R_(e)″ are as defined above), a M_(c)-SO₂—NR_(e)-group (M_(c) andR_(e) are as defined above) or a M_(c)R_(e)N—SO₂-group (M_(c) and R_(e)are as defined above), and R_(d) is as defined above];

-   (3) a Z group:-   a —N═C(Y_(a))—Y_(a)′-group (Y_(a) represents a hydrogen atom, or a    C1-C10 alkyl group optionally substituted with a halogen atom, or a    C1-C10 alkoxy group, and Y_(a)′ represents an oxy group, or a thio    group, or an imino group optionally substituted with a C1-C10 alkyl    group), a —Y_(b)—Y_(b)′—Y_(b)″-group (Y_(b) and Y_(b)′ are the same    or different, and represent a methylene group, or an oxy group, or a    thio group, or a sulfinyl group, or an imino group optionally    substituted with a C1-C10 alkyl group, and Y_(b)′ represents a C1-C4    alkylene group optionally substituted with a halogen atom, or a    C1-C4 alkylene group optionally having an oxo group) or a    —Y_(c)—O—Y_(c)′—O-group (Y_(c) and Y_(c)′ are the same or different,    and represent a C1-C10 alkylene group);-   III. Q_(A) represents a hydroxy group, a (b)-group ((b) is as    defined above), an A₉-B₆—B_(c)-group [A₉ represents a substituent of    the following A₇ group or A₈ group, B₆ represents a carbonyl group    or a thiocarbonyl group, and B_(c) represents an oxy group or a    —N((O)_(m)R₁)-group (m represents 0 or 1, and R₁ is as defined    above), provided that when A₉ is a hydrogen atom, then B_(c) is not    a sulfonyl group], an A₇″-SO₂—B_(c)-group (A₇″ represents a    substituent of the following A₇″ group, and B_(c) is as defined    above), an A₈-SO₂—B_(c)-group (A₈ represents a substituent of the    following A₈ group, and B_(c) is as defined above, provided that A₈    is not a hydrogen atom), a R₁R₁′N—SO₂—B_(c)-group (R₁ is as defined    above, R₁′ is the same as or different from R₁, and has the same    meaning as that of R₁, and B_(c) is as defined above), a    (b)-SO₂—B_(c)-group ((b) and B_(c) are as defined above), an    A₉′-B_(c)-group (A₉′ represents a substituent of the following A₇′    group or A₈′ group, and B_(c) is as defined above), a    D₅-R₄—B_(c)-group (D₅ represents a substituent of the following D₅    group, R₄ represents a C1-C10 alkylene group, and B_(c) is as    defined above), a M_(c)-B₃—B_(c)-group (B₃ represents a carbonyl    group, a thiocarbonyl group or a sulfonyl group, and M_(c) and B_(c)    are as defined above) or a M_(c)-B_(c)-group (M_(c) and B_(c) are as    defined above);-   (1) an A₇ group:

a C2-C10 alkenyl group optionally substituted with a halogen atom, aC2-C10 alkynyl group, a C3-C10 haloalkynyl group, a R₂—B₁—R₄-group (R₂and B₁ are as defined above, and R₄ is as defined above), a D₄-R₄-group(D₄ represents a substituent of the following D₄ group, and R₄ is asdefined above), a D₅-R₄-group (D₅ represents a substituent of thefollowing D₅ group, and R₄ is as defined above), a D₁-R₄-group {D₁represents a substituent of the following D₁ group, and R₄ is as definedabove}, a (b)-R₄-group ((b) is as defined above, and R₄ is as definedabove), a (c)-R₄-group ((c) is as defined above, and R₄ is as definedabove), a D₂-R₄-group {D₂ represents a substituent of the following D₂group, and R₄ is as defined above}, a D₃-R₄-group {D₃ represents asubstituent of the following D₃ group, and R₄ is as defined above}, anA₄-SO₂—R₄-group {A₄ represents a (b)-group ((b) is as defined above), a(c)-group ((c) is as defined above) or a R₁R₁′N-group (R₁ and R₁′ are asdefined above), and R₄ is as defined above} or an A₂-CO—R₄-group (A₂represents a substituent of the following A₂ group, and R₄ is as definedabove);

-   (2) an A₈ group: a hydrogen atom, or a C1-C10 alkyl group optionally    substituted with a halogen atom;-   (3) an A₇′ group: a C3-C10 alkenyl group optionally substituted with    a halogen atom, a C3-C10 alkynyl group optionally substituted with a    halogen atom, a R₂—B₁—R₄′-group (R₂ and B₁ are as defined above, and    R₄′ represents a C2-C10 alkylene group), a D₄-R₄′-group (D₄ and R₄′    are as defined above), a D₁-R₄′-group (D₁ and R₄′ are as defined    above), a (b)-R₄′-group ((b) and R₄′ are as defined above), a    (c)-R₄′-group ((c) and R₄′ are as defined above), a D₂-R₄-group (D₂    and R₄ are as defined above), a D₃-R₄′-group (D₃ and R₄′ are as    defined above) or an A₂-CO—R₄-group (A₂ and R₄ are as defined    above);-   (4) an A₈′ group: a C1-C10 alkyl group or a C2-C10 haloalkyl group;-   (5) an A₇″ group: a C2-C10 alkenyl group, a C3-C10 alkenyl group    substituted with a halogen atom, a C3-C10 alkynyl group optionally    substituted with a halogen atom, a R₂—B₁—R₄′-group (R₂, B₁ and R₄′    are as defined above), a D₄-R₄′-group (D₄ and R₄′ are as defined    above), a D₅-R₄-group (D₅ and R₄ are as defined above), a    D₁-R₄′-group (D₁ and R₄′ are as defined above), a (b)-R₄′-group ((b)    and R₄′ are as defined above), a (c)-R₄′-group ((c) and R₄′ are as    defined above), a D₂-R₄-group (D₂ and R₄ are as defined above), a    NO₂—R₄-group (R₄ is as defined above) or an A₂-CO—R₄-group (A₂ and    R₄ are as defined above);-   (i) a D₄ group: a hydroxy group or an A₁-O-group [A₁ represents a    R₃—(CHR₀)_(m)—(B₂—B₃)_(m)′-group {R₃ represents a hydrogen atom, or    a C1-C10 alkyl group optionally substituted with a halogen atom or a    R₂—B₁-group (R₂ and B₁ are as defined above), or a C2-C10 alkenyl    group, or a C2-C10 alkynyl group, R₀ represents a hydrogen atom, a    C1-C10 alkyl group or a C2-C10 haloalkyl group, m is as defined    above, B₂ represents a single bond, an oxy group, a thio group or a    —N((O)_(n)R₁′)-group (R₁′ is as defined above, and n represents 0 or    1), B₃ is as defined above, m′ represents 0 or 1 and, when B₃ is a    sulfonyl group, then m is 0, and R₃ is not a hydrogen atom}];-   (ii) a D₅ group: an O═C(R₃)-group (R₃ is as defined above), an    A₁-(O)_(n)—N═C(R₃)-group (A₁, n and R₃ are as defined above), a    R₁—B₀—CO—R₄—(O)_(n)—N═C(R₃)-group [R₁, R₄, n and R₃ are as defined    above, and B₀ represents an oxy group, a thio group or a    —N((O)_(m)R₁′)-group (R₁′ and m are as defined above)], a    D₂-R₄—(O)_(n)—N═C(R₃)-group (D₂, R₄, n and R₃ are as defined above)    or a R₁A₁N—N═C(R₃)-group (R₁, A₁ and R₃ are as defined above);-   (iii) a D₁ group: a (R₁—(O)_(k)-)A₁N—(O)_(k)′-group (R₁ and A₁ are    as defined above, and k and k′ are the same or different, and    represent 0 or 1);-   (iv) a D₂ group: a cyano group, a R₁R₁′NC(═N—(O)_(n)-A₁)-group (R₁,    R₁′, n and A₁ are as defined above), an A₁N═C(—OR₂)-group (A₁ and R₂    are as defined above) or a NH₂—CS-group;-   (v) a D₃ group: a nitro group or a R₁₀SO₂-group (R₁ is as defined    above);-   (vi) an A₂ group:-   1) an A₃-B₄-group-   [A₃ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10    haloalkyl group, or a C2-C10 alkenyl group optionally substituted    with a halogen atom, or a C3-C10 alkynyl group optionally    substituted with a halogen atom, or a R_(a)—(R₄)_(m)-group (R_(a)    represents a phenyl group, a pyridyl group, a furyl group or a    thienyl group, optionally substituted with a halogen atom, a C1-C10    alkyl group, a C1-C10 alkoxy group or a nitro group, and R₄ and m    are as defined above), or a C1-C10 alkyl group substituted with a    (b)-R₄-group ((b) and R₄ are as defined above), a (c)-R₄-group ((c)    and R₄ are as defined above), a R₂—B₁—R₄-group (R₂, B₁ and R₄ are as    defined above), a D₄-R₄-group (D₄ and R₄ are as defined above), a    D₅-group (D₅ is as defined above), a D₁-R₄-group (D₁ and R₄ are as    defined above), a D₂-group (D₂ is as defined above), a D₃-R₄-group    (D₃ and R₄ are as defined above) or an A₄-SO₂—R₄-group {A₄ is as    defined above, and R₄ is as defined above},

B₄ represents an oxy group, a thio group or a —N((O)_(n)R₁)-group (R₁and m are as defined above), provided that when B₄ is a thio group, thenA₃ is not a hydrogen atom];

-   2) a R₁—B₄—CO—R₄—B₄′-group (R₁, B₄ and R₄ are as defined above, B₄′    is the same as or different from B₄, and has the same meaning as    that of B₄, provided that when B₄ is a thio group, then R₂ is not a    hydrogen atom) or a D₂-R₄—B₄-group (D₂, R₄ and B₄ are as defined    above);-   3) a R₂—SO₂—NR₁-group (R₂ is as defined above, provided that a    hydrogen atom is excluded, and R₁ is as defined above);-   4) a (b)-group ((b) is as defined above);-   5) a (c)-group ((c) is as defined above) or-   6) a R₁A₁N—NR₁′-group (R₁, A₁ and R₁′ are as defined above);-   IV. T_(A) represents a hydrogen atom, an A₉′-group (A₉′ is as    defined above), a D₅-R₄-group (D₅ and R₄ are as defined above) or a    M_(c)-group (M_(c) is as defined above);-   V. M_(a)′ is the same as or different from M_(a), and has the same    meaning as that of M_(a), and r represents 0, 1, 2, 3 or 4; and

the “as defined above” in the same symbol between a plurality ofsubstituents indicates that the plurality of substituents independentlyrepresent the same meaning as that described above and, between theplurality of substituents, a selection range of selected substituents isthe same, while the selected substituents may be the same or differentas far as they are selected in the range]; and an inert carrier;

20. A 2(1H)-pyridinone compound represented by the formula (XX):

[wherein

-   I. A represents a benzene ring or a pyridine ring;-   II. In (X_(h))_(p), X_(h) represents a hydroxy group, a halogen    atom, a C1-C10 alkyl group, a C1-C10 alkoxycarbonyl group, a    (R′)₂N-group (R′ represents a C1-C10 alkyl group), a nitro group or    a C1-C10 alkoxy group, p represents 0, 1, 2, 3 or 4 and, when p is 2    or more, X_(h)'s are the same or different, provided that when p is    2 or more, and in case that X_(h) is selected from a hydroxy group,    a halogen atom, a C1-C10 alkyl group and a C1-C10 alkoxy group, then    X_(h)'s do not represent the same group or atom at the same time;-   III. In (Y_(h))_(q), Y_(h) is a substituent on a carbon atom, and    represents a substituent of the following X₇ group or Y₇ group, q    represents 0, 1, 2, 3, 4 or 5, when q is 2 or more, Y_(h)'s are the    same or different and, when q is 2 or more, the adjacent two same or    different Y_(h)'s constitute a group of a Z₇ group, and may be fused    with an A ring;-   (1) a X₇ group:-   a M_(a)-group [M_(a) represents a R_(b)-group (R_(b) represents a    C1-C10 alkyl group optionally substituted with a halogen atom), a    halogen atom, a nitro group, a cyano group, a hydroxy group, a    R_(c)—B_(a)—R_(d)-group (R_(c) represents a C1-C10 alkyl group    optionally substituted with a halogen atom, B_(a) represents an oxy    group, a thio group, a sulfinyl group or a sulfonyl group, and R_(d)    represents a single bond or a C1-C10 alkylene group), a    HOR_(d)-group (R_(d) is as defined above), a R_(e)—CO—R_(d)-group    (R_(e) represents a hydrogen atom, or a C1-C10 alkyl group    optionally substituted with a halogen atom, and R_(d) is as defined    above), a R_(e)—CO—O—R_(d)-group (R_(e) and R_(d) are as defined    above), a R_(e)O—CO—R_(d)-group (R_(e) and R_(d) are as defined    above), a HO—CO—CH═CH-group, a R_(e)R_(e)′N—R_(d)-group (R_(e) and    R_(e)′ are the same or different, R_(e) is as defined above, R_(e)′    has the same meaning as that of R_(e), and R_(d) is as defined    above), a R_(e)—CO—NR_(e)′—R_(d)-group (R_(e), R_(e)′ and R_(d) are    as defined above), a R_(b)O—CO—N(R_(e))—R_(d)-group (R_(b), R_(e)    and R_(d) are as defined above), a R_(e)R_(e)′N—CO—R_(d)-group    (R_(e), R_(e)′ and R_(d) are as defined above), a    R_(e)R_(e)′N—CO—NR_(e)″—R_(d)-group (R_(e), R_(e)′ and R_(e)″ are    the same or different, R_(e) and R_(e)′ are as defined above, R_(e)″    has the same meaning as that of R_(e), and R_(d) is as defined    above), a R_(e)R_(e)″N—C(═NR_(e)″)—NR_(e)′″—R_(d)-group (R_(e),    R_(e)′, R_(e)″ and R_(e)′″ are the same or different, R_(e), R_(e)′    and R_(e)″ are as defined above, R_(e)′″ has the same meaning as    that of R_(e), and R_(d) is as defined above), a    R_(b)—SO₂—NR_(e)—R_(d)-group (R_(b), R_(e) and R_(d) are as defined    above), a R_(e)R_(e)′N—SO₂—R_(d)-group (R_(e), R_(e)′ and R_(d) are    as defined above), a C2-C10 alkenyl group or a C2-C10 alkynyl    group], provided that when A represents a benzene ring, then a    X_(h)-group (X_(h) is as defined above) is excluded;-   (2) a Y₇ group:-   a M_(b)-R_(d)-group [M_(b) represents a M_(c)-group {M_(c)    represents a M_(d)-R_(d)′-group {M_(d) represents a phenyl group    optionally substituted with a M_(a)-group (M_(a) is as defined    above), or a pyridyl group optionally substituted with a M_(a)-group    (M_(a) is as defined above), or a naphthyl group optionally    substituted with a M_(a)-group (M_(a) is as defined above), or

a (b)-group {in (b), G₁, G₂, G₄ and G₅ represent a methylene group whichis connected to an adjacent atom with a single bond, and may besubstituted with a methyl group, or a methine group which is connectedto an adjacent atom with a double bond, and may be substituted with amethyl group, and G₃ represents a single bond, or a double bond, or aC1-C10 alkylene group optionally substituted with a methyl group, an oxygroup, a thio group, a sulfinyl group, a sulfonyl group or a —NR₁-group{R₁ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10alkyl group substituted with a halogen atom or a R₂—B₁-group (R₂represents a C1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10alkynyl group, and B₁ represents an oxy group, a thio group, a sulfinylgroup or a sulfonyl group), or a C3-C10 alkenyl group, or a C3-C10alkynyl group), or a C2-C10 alkenylene group optionally substituted witha methyl group, an oxy group, a thio group, a sulfinyl group, a sulfonylgroup or a —NR₁-group (R₁ is as defined above)},

a (c)-group (in (c), J₁, J₂ and J₃ are the same or different, andrepresent a methine group optionally substituted with a methyl group, ora nitrogen atom),

a (d)-group (l is 2, 3 or 4, and B_(b) represents an oxy group or a thiogroup)or

an (e)-group (l and B_(b) are as defined above), R_(d)′ is the same asor different from R_(d), and has the same meaning as that of R_(d)}}, aM_(c)-B_(a)-group (M_(c) and B_(a) are as defined above), aM_(c)-CO-group (M_(c) is as defined above), a M_(c)-CO—O-group (M_(c) isas defined above), a M_(c)O—CO-group (M_(c) is as defined above), aM_(c)R_(e)N-group (M_(c) and R_(e) are as defined above), aM_(c)-CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)O—CO—NR_(e)-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO-group (M_(c) and R_(e) are as defined above), aM_(c)R_(e)N—CO—NR_(e)′-group (M_(c), R_(e) and R_(e)′ are as definedabove), a M_(c)R_(e)N—C(═NR_(e)′)—NR_(e)″-group (M_(c), R_(e), R_(e)′and R_(e)″ are as defined above), a M_(c)-SO₂—NR_(e)-group (M_(c) andR_(e) are as defined above) or a M_(c)R_(e)N—SO₂-group (M_(c) and R_(e)are as defined above), and R_(d) is as defined above];

-   (3) a Z₇ group:-   a —N═C(Y_(a))—Y_(a)′-group (Y_(a) represents a hydrogen atom, or a    C1-C10 alkyl group optionally substituted with a halogen atom, or a    C1-C10 alkoxy group, and Y_(a)′ represents an oxy group, or a thio    group, or an imino group optionally substituted with a C1-C10 alkyl    group), a —Y_(b)—Y_(b)′—Y_(b)″-group (Y_(b) and Y_(b)″ are the same    or different, and represent a methylene group, or an oxy group, or a    thio group, or a sulfinyl group, or an imino group optionally    substituted with a C1-C10 alkyl group, and Y_(b)′ represents a C1-C4    alkylene group optionally substituted with a halogen atom or a C1-C4    alkylene group optionally having an oxo group) or a    —Y_(c)—O—Y_(c)′—O-group (Y_(c) and Y_(c)′ are the same or different,    or a C1-C10 alkylene group), provided that when p is 0, then Y_(h)    does not fused with an A ring to form a benzo[1,3]dioxol ring;-   IV. Q_(A) represents a hydroxy group, a (b)-group ((b) is as defined    above), an A₉-B₆—B_(c)-group [A₉ represents a substituent of the    following A₇ group or A₈ group, B₆ represents a carbonyl group or a    thiocarbonyl group, and B_(c) represents an oxy group or a    —N((O)_(m)R₁-group (m represents 0 or 1, and R₁ is as defined    above), provided that when A₉ is a hydrogen atom, then B_(c) is not    a sulfonyl group], an A₇″-SO₂—B_(c)-group (A₇″ represents a    substituent of the following A₇″ group, and B_(c) is as defined    above), an A₈-SO₂—B_(c)-group (A₈ represents a substituent of the    following A₈ group, and B_(c) is as defined above, provided that A₈    is not a hydrogen atom), a R₁R₁′N—SO₂—B_(c)-group (R₁ is as defined    above, R₁′ is the same as or different from R₁, and has the same    meaning as that of R₁, and B_(c) is as defined above), a    (b)-SO₂—B_(c)-group ((b) and B_(c) are as defined above), an    A₉′-B_(c)-group (A₉′ represents a substituent of the following A₇′    group or A₈′ group, and B_(c) is as defined above), a    D₅-R₄—B_(c)-group (D₅ represents a substituent of the following D₅    group, R₄ represents a C1-C10 alkylene group, and B_(c) is as    defined above), a M_(c)-B₃—B_(c)-group (B₃ represents a carbonyl    group, a thiocarbonyl group or a sulfonyl group, and M_(c) and B_(c)    are as defined above) or a M_(c)-B_(c)-group (M_(c) and B_(c) are as    defined above);-   (1) an A₇ group:-   a C2-C10 alkenyl group optionally substituted with a halogen atom, a    C2-C10 alkynyl group, a C3-C10 haloalkynyl group, a R₂—B₁—R₄-group    (R₂ and B₁ are as defined above, and R₄ is as defined above), a    D₄-R₄-group (D₄ represents a substituent of the following D₄ group,    and R₄ is as defined above), a D₅-R₄-group (D₅ represents a    substituent of the following D₅ group, and R₄ is as defined above),    a D₁-R₄-group {D₁ represents a substituent of the following D₁    group, and R₄ is as defined above}, a (b)-R₄-group ((b) is as    defined above, and R₄ is as defined above), a (c)-R₄-group ((c) is    as defined above, and R₄ is as defined above), a D₂-R₄-group {D₂    represents a substituent of the following D₂ group, and R₄ is as    defined above}, a D₃-R₄-group {D₃ represents a substituent of the    following D₃ group, and R₄ is as defined above}, an A₄-SO₂—R₄-group    {A₄ represents a (b)-group ((b) is as defined above), a (c)-group    ((c) is as defined above) or a R₁R₁′-N-group (R₁ and R₁′ are as    defined above), and R₄ is as defined above) or an A₂-CO₂—R₄-group    (A₂ represents a substituent of the following A₂ group, and R₄ is as    defined above);-   (2) an A₈ group: a hydrogen atom, or a C1-C10 alkyl group optionally    substituted with a halogen atom;-   (3) an A₇′ group: a C3-C10 alkenyl group optionally substituted with    a halogen atom, a C3-C10 alkynyl group optionally substituted with a    halogen atom, a R₂—B₁—R₄′-group (R₂ and B₁ are as defined above, and    R₄′ represents a C2-C10 alkylene group), a D₄-R₄′-group (D₄ and R₄′    are as defined above), a D₁-R₄′-group (D₁ and R₄′ are as defined    above), a (b)-R₄′-group ((b) and R₄′ are as defined above), a    (c)-R₄′-group ((c) and R₄′ are as defined above), a D₂-R₄-group (D₂    and R₄ are as defined above), a D₃-R₄′-group (D₃ and R₄′ are as    defined above) or an A₂-CO—R₄-group (A₂ and R₄ are as defined    above);-   (4) an A₈′ group: a C1-C10 alkyl group or a C2-C10 haloalkyl group;-   (5) an A₇″ group: a C2-C10 alkenyl group, a C3-C10 alkenyl group    substituted with a halogen atom, a C3-C10 alkynyl group optionally    substituted with a halogen atom, a R₂—B₁—R₄′-group (R₂, B₁ and R₄′    are as defined above), a D₄-R₄′-group (D₄ and R₄′ are as defined    above), a D₅-R₄-group (D₅ and R₄ are as defined above), a    D₁-R₄′-group (D₁ and R₄′ are as defined above), a (b)-R₄′-group ((b)    and R₄′ are as defined above), a (c)-R₄′-group ((c) and R₄′ are as    defined above), a D₂-R₄-group (D₂ and R₄ are as defined above), a    NO₂—R₄-group (R₄ is as defined above) or an A₂-CO—R₄-group (A₂ and    R₄ are as defined above);-   (i) a D₄ group: a hydroxy group or an A₁-O-group [A₁ represents a    R₃—(CHR₀)_(m)—(B₂—B₃)_(m)′-group {R₃ represents a hydrogen atom, or    a C1-C10 alkyl group optionally substituted with a halogen atom or a    R₂—B₁-group (R₂ and B₁ are as defined above), or a C2-C10 alkenyl    group, or a C2-C10 alkynyl group, R₀ represents a hydrogen atom, a    C1-C10 alkyl group or a C2-C10 haloalkyl group, m is as defined    above, B₂ represents a single bond, an oxy group, a thio group or a    —N((O)_(n)R₁′)-group (R₁′ is as defined above, and n represents 0 or    1), B₃ is as defined above, m′ represents 0 or 1 and, when B₃ is a    sulfonyl group, then m is 0, and R₃ is not a hydrogen atom}];-   (ii) a D₅ group: an O═C(R₃)-group (R₃ is as defined above), an    A₁-(O)_(n)—N═C(R₃)-group (A₁, N and R₃ are as defined above), a    R₁—B₀—CO—R₄—(O)_(n)—N═C(R₃)-group [R₁, R₄, n and R₃ are as defined    above, and B₀ represents an oxy group, a thio group or a    —N((O)_(m)R₁′)-group (R₁′ and m are as defined above)], a    D₂-R₄—(O)_(n)—N═C(R₃)-group (D₂, R₄, n and R₃ are as defined above)    or a R₁A₁N—N═C(R₃)-group (R₁, A₁ and R₃ are as defined above);-   (iii) a D₁ group: a (R₁—O)_(k)-)A₁N—(O)_(k)′-group (R₁ and A₁ are as    defined above, and k and k′ are the same or different, and represent    0 or 1);-   (iv) a D₂ group: a cyano group, a R₁R₁′NC(═N—(O)_(n)-A₁-group (R₁,    R₁′, N and A₁ are as defined above), an A₁N═C(—OR₂)-group (A₁ and R₂    are as defined above) or a NH₂—CS-group;-   (v) a D₃ group: a nitro group or a R₁OSO₂-group (R₁ is as defined    above);-   (vi) an A₂ group:-   1) an A₃-B₄-group-   [A₃ represents a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10    haloalkyl group, or a C2-C10 alkynyl group optionally substituted    with a halogen atom, or a C3-C10 alkynyl group optionally    substituted with a halogen atom, or a R_(a)—(R₄)_(m)-group (R_(a)    represents a phenyl group, a pyridyl group, a furyl group or a    thienyl group, optionally substituted with a halogen atom, a C1-C10    alkyl group, a C1-C10 alkoxy group or a nitro group, and R₄ and m    are as defined above), or a C1-C10 alkyl group substituted with a    (b)-R₄-group ((b) and R₄ are as defined above), a (c)-R₄-group ((c)    and R₄ are as defined above), a R₂—B₁—R₄-group (R₂, B₁ and R₄ are as    defined above), a D₄-R₄-group (D₄ and R₄ are as defined above), a    D₅-group (D₅ is as defined above), a D₁-R₄-group (D₁ and R₄ are as    defined above), a D₂-group (D₂ is as defined above), a D₃-R₄-group    (D₃ and R₄ are as defined above) or an A₄-SO₂—R₄-group {A₄ is as    defined above, and R₄ is as defined above},

B₄ represents an oxy group, a thio group or a —N((O)_(m)R₁)-group (R₁and m are as defined above), provide that when A₄ is a thio group, thenA₃ is not a hydrogen atom];

-   2) a R₁—B₄—CO—R₄—B₄′-group (R₁, B₄ and R₄ are as defined above, B₄′    is the same as or different from B₄, and has the same meaning as B₄,    provided that when B₄ is a thio group, then R₂ is not a hydrogen    atom) or a D₂-R₄—B₄-group (D₂, R₄ and B₄ are as defined above);-   3) a R₂—SO₂—NR₁-group (R₂ is as defined above, provided that a    hydrogen atom is excluded, and R₁ is as defined above);-   4) a (b)-group ((b) is as defined above);-   5) a (c)-group ((c) is as defined above) or-   6) a R₁A₁N—NR₁′-group (R₁, A₁ and R₁′ are as defined above);-   V. T_(A) represents a hydrogen atom, an A₉′-group (A₉′ is as defined    above), a D₅-R₄-group (D₅ and R₄ are as defined above) or a    M_(c)-group (M_(c) is as defined above);-   VI. M_(a)′ is the same as or different from M_(a), and has the same    meaning as that of M_(a), and r represents 0, 1, 2, 3 or 4, provided    that when an A ring is a benzene ring, then q is not 0 and, when an    A ring is a benzene ring or a pyridine ring, then p and q are not 0    at the same time, in either case; and

the “as defined above” in the same symbol between a plurality ofsubstituents indicates that the plurality of substituents independentlyrepresent the same meaning as that described above and, between theplurality of substituents, a selection range of selected substituents isthe same, while the selected substituents may be the same or differentas far as they are selected in the range];

21. A I type collagen gene transcription suppressing composition, whichcomprises a 2(1H)-quinolinone compound represented by the formula (XXI):

[wherein X_(IV) represents a hydrogen atom, or a hydroxy group, or ahalogen atom, or a C1-C4 alkyl group optionally substituted with ahalogen atom or a C1-C4 alkoxy group, or a C2-C4 alkenyl group, or aC2-C4 alkynyl group, or a C1-C4 alkoxy group, or a R_(I)—S(O)_(l)-group(R_(I) represents a C1-C4 alkyl group, and l represents an integer of 0to 2), or a nitro group, or a cyano group, or a carboxy group, or aC1-C4 alkoxycarbonyl group, or a (R_(I))₂N-group (R_(I) is as definedabove), or a R_(I)—CO—NH-group (R_(I) is as defined above), or aR_(I)—O—CO—NH-group (R₁ is as defined above), or a R_(I)NH—CO—NH-group(R_(I) is as defined above), or a (R_(I)′)₂N—CO-group (R_(I)′ representsa hydrogen atom or a C1-C4 alkyl group), or a RB-group (B represents anoxygen atom or a sulfur atom, and R represents a C1-C4 alkyl groupsubstituted with a halogen atom), k represents an integer of 1 to 4 and,when k is an integer of 2 to 4, X_(IV)'s may be different, and r_(II)and r_(II)′ are the same or different, and represent a hydrogen atom ora C1-C4 alkyl group];

-   and an inert carrier;

22. A 2(1H)-quinolinone compound represented by the formula (XXII):

[wherein X_(IV)′ represents a C2-C4 alkyl group, or a C1-C4 alkyl groupsubstituted with a halogen atom or a C1-C4 alkoxy group, or a C2-C4alkenyl group, or a C2-C4 alkynyl group, or a C2-C4 alkoxy group, or aR_(I)—S(O)_(l)-group (R_(I) represents a C1-C4 alkyl group, and lrepresents an integer of 0 to 2), or a cyano group, or a carboxy group,or a C2-C4 alkoxycarbonyl group, or a (R_(II))₂N-group (R_(II)represents a C2-C4 alkyl group), or a R_(I)—CO—NH-group (R_(I) is asdefined above), or a R_(I)O—CO—NH-group (R_(I) is as defined above), ora R_(I)NH—CO—NH-group (R_(I) is as defined above), or a(R_(I)′)₂N—CO-group (R_(I)′ represents a hydrogen atom or a C1-C4 alkylgroup), or a RB-group (B represents an oxygen atom or a sulfur atom, andR represents a C1-C4 alkyl group substituted with a halogen atom),X_(IV)″ represents a hydrogen atom, a halogen atom, a C1-C4 alkyl groupor a C1-C4 alkoxy group, m represents 1 or 2 and, when m is 2, X_(IV)″'smay be different, and r_(II) and r_(II)′ are the same or different, andrepresent a hydrogen atom or a C1-C4alkyl group]

23. Use of a compound according to the above item 5, 6, 8, 9, 11, 12,13, 14, 16, 18, 20 or 22, as an active ingredient for suppressingtranscription of a Type I collagen gene;

24. Use of a compound according to the above item 5, 6, 8, 9, 11, 12,13, 14, 16, 18, 20 or 22, as an active ingredient for decreasingexpression of a Type I collagen gene to induce a reduction inaccumulation of collagen and thereby improving tissue fibrosis;

25. A composition for improving tissue fibrosis, which comprises acompound according to the above item 5, 6, 8, 9, 11, 12, 13, 14, 16, 18,20 or 22, and an inert carrier;

26. A method for improving tissue fibrosis, which comprisesadministering an effective amount of a compound according to the aboveitem 5, 6, 8, 9, 11, 12, 13, 14, 16, 18, 20 or 22 to a mammal in needthereof;

27. Use of a compound according to the above item 5, 6, 8, 9, 11, 12,13, 14, 16, 18, 20 or 22, as an active ingredient for suppressing theactivity of TGF-β;

28. A composition for suppressing the activity of TGF-β, which comprisesa compound according to the above item 5, 6, 8, 9, 11, 12, 13, 14, 16,18, 20 or 22, and an inert carrier;

29. Use of a compound according to the above item 5, 6, 8, 9, 11, 12,13, 14, 16, 18, 20 or 22, as an active ingredient for inhibiting apromoting effect of TGF-β on transition to a hair regression phase toinduce extension of a hair growth phase and thereby providinghair-growing effect;

30. A composition for hair growth which comprises a compound accordingto the above item 5, 6, 8, 9, 11, 12, 13, 14, 16, 18, 20 or 22, and aninert carrier;

31. A method for growing hair, which comprises administering aneffective amount of a compound according to the above item 5, 6, 8, 9,11, 12, 13, 14, 16, 18, 20 or 22 to a mammal in need thereof;

32. Use of a compound according to the above item 1, 2, 3, 4, 7, 10, 15,17, 19 or 21, as an active ingredient for suppressing transcription of aType I collagen gene;

33. Use of a compound according to the above item 1, 2, 3, 4, 7, 10, 15,17, 19 or 21, as an active ingredient for decreasing expression of aType I collagen gene to induce a reduction in accumulation of collagenand thereby improving tissue fibrosis;

34. A composition for improving tissue fibrosis, which comprises acompound according to the above item 1, 2, 3, 4, 7, 10, 15, 17, 19 or21, and an inert carrier;

35. A method for improving tissue fibrosis, which comprisesadministering an effective amount of a compound according to the aboveitem 1, 2, 3, 4, 7, 10, 15, 17, 19 or 21 to a mammal in need thereof;

36. Use of a compound according to the above item 1, 2, 3, 4, 7, 10, 15,17, 19 or 21, as an active ingredient for suppressing the activity ofTGF-β;

37. A composition for suppressing the activity of TGF-β, which comprisesa compound according to the above item 1, 2, 3, 4, 7, 10, 15, 17, 19 or21, and an inert carrier;

38. Use of a compound according to the above item 1, 2, 3, 4, 7, 10, 15,17, 19 or 21, as an active ingredient for inhibiting a promoting effectof TGF-β on transition to a hair regression phase to induce extension ofa hair growth phase and thereby providing hair-growing effect;

39. A composition for hair growth which comprises a compound accordingto the above item 1, 2, 3, 4, 7, 10, 15, 17, 19 or 21, and an inertcarrier;

40. A method for growing hair, which comprises administering aneffective amount of a compound according to the above item 1, 2, 3, 4,7, 10, 15, 17, 19 or 21 to a mammal in need thereof;

41. A 2(1H)-pyridinone compound represented by the formula (XXIII):

42. A 2(1H)-pyridinone compound represented by the formula (XXIV):

-   -   and the like.

BEST MODE FOR CARRYING OUT THE INVENTION

The present invention will be explained in detail below.

In the present invention, a saturated hydrocarbon group in an alkylgroup, a haloalkyl group, an alkoxy group, an alkoxycarbonyl group, analkylthio group, an alkylsulfinyl group, an alkylsulfonyl group and analkylene group may be branched, and a part or all of carbon atomsthereof may form a ring. An unsaturated hydrocarbon group in an alkenylgroup, an alkenyloxy group, an alkynyl group, an alkynyloxy group and analkenylene group may have a branch, and a part or all of carbon atomsthereof may form a ring, and the number of unsaturated bonds is singularor plural.

In the present invention, examples of an alkyl group include a methylgroup, an ethyl group, an isopropyl group, a cyclohexyl group, acyclopropylmethyl group and the like, examples of a haloalkyl groupinclude a 2,2,2-trifluoroethyl group and the like, examples of an alkoxygroup include a methoxy group, an ethoxy group, a cyclopentyloxy group,a 2-cyclohexylethoxy group and the like, examples of an alkylthio groupinclude a methylthio group and the like, examples of an alkylsulfinylgroup include a methylsulfinyl group and the like, examples of analkylsulfonyl group include a methylsulfonyl group and the like,examples of an alkylene group include a methylene group, anethylethylene group, a 1,4-cyclohexylene group and the like, examples ofan alkenyl group include a vinyl group, a 2-propenyl group, a3-methyl-2-butenyl group, a 1,3-butadienyl group, a 3-cyclohexenyl groupand the like, examples of an alkynyl group include an ethynyl group, a2-propynyl group, a 2-penten-4-ynyl and the like, and examples of analkenylene group include a vinylene group, a propenylene group, a1,3-butadienylene group and the like.

In the present invention, examples of a halogen atom include a fluorineatom, a chlorine atom, a bromine atom and an iodine atom.

In the present invention, a pyridyl group includes a 2-pyridyl group, a3-pyridyl group and a 4-pyridyl group, a furyl group includes a 2-furylgroup and a 3-furyl group, a thienyl group includes a 2-thienyl groupand a 3-thienyl group, and a naphthyl group includes a 1-naphthyl groupand a 2-naphthyl group.

In the present invention, examples of a leaving group include analkylsulfonyloxy group such as a mesyloxy group and the like, anarylsulfonyloxy group such as a tosyloxy group and the like, analkoxysulfonyloxy group such as a methoxysulfonyloxy group and the like,and a halogen atom such as a bromine atom and the like.

In a cinnamoyl compound represented by the formulas (I) to (III)(hereinafter, referred to as the present compounds (I) to (III),respectively, in some cases), a 2H-pyran-2-one compound represented bythe formula (IV) and (V) (hereinafter, referred to as the presentcompound (IV) and (V), respectively, in some cases), a 2H-pyran-2-onecompound represented by the formula (VI) (hereinafter, referred to asthe present intermediate (VI) in some cases), a 2H-1-benzopyran-2-onecompound represented by the formulas (X) and (XI) (hereinafter, referredto as the present compounds (X) and (XI), respectively, in some cases),a 2H-1-benzopyran-2-one compound represented by the formula (XII)(hereinafter, referred to as the present intermediate (XII) in somecases), a 2(1H)-pyridinone compound represented by the formulas (XV) and(XVI) (hereinafter, referred to as the present compounds (XV) and (XVI),respectively, in some cases) and a 2(1H)-quinolinone compoundrepresented by the formulas (XIX) and (XX) (hereinafter, referred to asthe present compounds (XIX) and (XX), respectively, in some cases), whenan A ring is a pyridine ring, a N-oxide thereof is also included.

The present compounds (I) to (V), (VII), (VIII), (X), (XI), (XIII), and(XV) to (XXII) (hereinafter, collectively referred to as the presentcompound in some cases) represents a pharmacologically acceptable saltthereof at the same time. A pharmacologically acceptable salt representsa salt with an inorganic acid, a salt with an organic acid, a salt withan inorganic base or a salt with an organic base, of the presentcompound. Examples of a salt with an inorganic acid includehydrochloride, hydrobromide and the like, examples of a salt with anorganic acid include acetate, benzoate and the like, examples of a saltwith an inorganic base include a potassium salt, a sodium salt and thelike, and examples of a base with an organic base include a pyridinesalt, a morpholine salt and the like.

Y_(A0), Q_(A0), K_(A0), L_(A0) and T_(A0) in the present compound (II)are independently represented by groups represented by D₁, D₂, D₃, D₄,D₅, R₀, R₁, R₁′, R₂, R₃, R₄, R₄′, A₁, A₂, A₃, A₄, A₇, A₇′, A₇″, A₈, A₈′,A₉, A₉′, B₀, B₁, B₂, B₃, B₄, B₄′, B₆, (b₀), (c₀), (d₀), (e₀), M_(a),M_(a)′, M_(a)″, M_(a)′″, M_(a)″″, M_(b0), M_(c0), M_(d0), R_(a0), R_(b),R_(c), R_(d), R_(d)′, R_(e), R_(e)′, R_(e)″, R_(e)′″, B_(a), B_(b),B_(c), Y_(a), Y_(a)′, Y_(b), Y_(b)′, Y_(b)″, Y_(c) and Y_(c)′, andintegers represented by k, k′, l, m, m′ and n.

Y_(A), Q_(A), K_(A), L_(A) and T_(A) in the present compound (III) areindependently represented by groups represented by D₁, D₂, D₃, D₄, D₅,R₀, R₁, R₁′, R₂, R₃, R₄, R₄′, A₁, A₂, A₃, A₄, A₇, A₇′, A₇″, A₈, A₈′, A₉,A₉′, B₀, B₁, B₂, B₃, B₄, B₄′, B₆, (b), (c), (d), (e), M_(a), M_(a)′,M_(a)″, M_(a)′″, M_(a)″″, M_(b), M_(c), M_(d), R_(a), R_(b), R_(c),R_(d), R_(d)′, R_(e), R_(e)′, R_(e)″, R_(e)′″, B_(a), B_(b), B_(c),Y_(a), Y_(a)′, Y_(b), Y_(b)′, Y_(b)″, Y_(c) and Y_(c)′, and integersrepresented by k, k′, l, m, m′ and n.

X_(a), Y_(a), X_(b), Y_(b), X_(c), Y_(c), Q_(A), Q_(A)′ and L_(a) in thepresent compounds (IV) and (V), and the present intermediate (VI) areindependently represented by groups represented by D₁, D₂, D₃, D₄, D₅,R₀, R₁, R₁′, R₂, R₃, R₄, R₄′, A₁, A₂, A₃, A₄, A₇, A₇′, A₇″, A₈, A₈′, A₉,A₉′, B₀, B₁, B₂, B₃, B₄, B₄′, B₆, (b), (c), (d), (e), M_(a), M_(a)′,M_(a)″, M_(a)′″, M_(a)″″, M_(b), M_(c), M_(d), R_(a), R_(b), R_(c),R_(d), R_(d)′, R_(e), R_(e)′, R_(e)″, R_(e)′″, B_(a), B_(b), B_(c),Y_(a), Y_(a)′, Y_(b), Y_(b)′, Y_(b)″, Y_(c) and Y_(c)′, and integersrepresented by k, k′, l, m, m′ and n.

X_(d), Y_(d), X_(e), Y_(e), Q_(A), Q_(A)′ and M_(a)′ in the presentcompounds (X) and (XI) and the present intermediate (XII) areindependently represented by groups represented by D₁, D₂, D₃, D₄, D₅,R₀, R₁, R₁′, R₂, R₃, R₄, R₄′, A₁, A₂, A₃, A₄, A₇, A₇′, A₇″, A₈, A₈′, A₉,A₉′, B₀, B₁, B₂, B₃, B₄, B₄′, B₆, (b), (c), (d), (e), M_(a), M_(a)′,M_(a)″, M_(a)′″, M_(a)″″, M_(b), M_(c), M_(d), R_(a), R_(b), R_(c),R_(d), R_(d)′, R_(e), R_(e)′, R_(e)″, R_(e)′″, B_(a), B_(b), B_(c),Y_(a), Y_(a)′, Y_(b), Y_(b)′, Y_(b)″, Y_(c) and Y_(c)′, and integersrepresented by k, k′, l, m, m′ and n.

Y_(f), X_(g), Y_(g), Q_(A), T_(A) and L_(a) in the present compounds(XV) and (XVI) are independently represented by groups represented byD₁, D₂, D₃, D₄, D₅, R₀, R₁, R₁′, R₂, R₃, R₄, R₄′, A₁, A₂, A₃, A₄, A₇,A₇′, A₇″, A₈, A₈′, A₉, A₉′, B₀, B₁, B₂, B₃, B₄, B₄′, B₆, (b), (c), (d),(e), M_(a), M_(a)′, M_(a)″, M_(a)′″, M_(a)″″, M_(b), M_(c), M_(d),R_(a), R_(b), R_(c), R_(d), R_(d)′, R_(e), R_(e)′, R_(e)″, R_(e)′″,B_(a), B_(b), B_(c), Y_(a), Y_(a)′, Y_(b), Y_(b)′, Y_(b)″, Y_(c) andY_(c)″, and integers represented by k, k′, l, m, m′ and n.

Y_(f), X_(h), Y_(h), Q_(A), T_(A) and M_(a)′ in the present compounds(XIX) and (XX) are independently represented by groups represented byD₁, D₂, D₃, D₄, D₅, R₀, R₁, R₁′, R₂, R₃, R₄, R₄′, A₁, A₂, A₃, A₄, A₇,A₇′, A₇″, A₈, A₈′, A₉, A₉′, B₀, B₁, B₂, B₃, B₄, B₄′, B₆, (b), (c), (d),(e), M_(a), M_(a)′, M_(a)″, M_(a)′″, M_(a)″″, M_(b), M_(c), M_(d),R_(a), R_(b), R_(c), R_(d), R_(d)′, R_(e), R_(e)′, R_(e)″, R′″, B_(a),B_(b), B_(c), Y_(a), Y_(a)′, Y_(b), Y_(b)′, Y_(b)″, Y_(c) and Y_(c)′ andintegers represented by k, k′, l, m, m′ and n.

In the substituent Y₀ group which can be taken by Y_(a) of the presentcompound (I), the “6 to 10-membered aryl group” represents a groupsconstituting a monocyclic or fused aromatic hydrocarbon group, andexamples include a phenyl group, a 1-naphthyl group, a 2-naphthyl group,a 6-indanyl group and the like, the “5 to 10-membered heteroaryl group”represents a group constituting a monocyclic or fused aromaticheterocycle, and examples include a 2-furyl group, a 3-furyl group, a2-thienyl group, a 3-thienyl group, a 2-pyridyl group, a 3-pyridylgroup, a 4-pyridyl group, a 2-quinolyl group and the like, and “a groupconstituting 3 to 10-membered hydrocarbon ring or heterocycle optionallycontaining an unsaturated bond” includes a monocycle or a fused cycle,and examples include a 2-cyclohexenyl group, a 2-morpholinyl group, a4-piperidyl group and the like, and these may be substituted with asingle or same or different plural aforementioned M_(a)-groups.

In the substituent Z₀ group which can be taken by Y_(a) of the presentcompound (I), “a group which is fused with an A ring” may have single orthe same or different plural atoms or groups selected from a halogenatom, a C1-C10 alkoxy group, a C3-C10 alkenyloxy group, a C3-C10alkynyloxy group, a carbonyl group, a thiocarbonyl group, an oxy group,a thio group, a sulfinyl group and a sulfonyl group.

In (d₀) of the substituent Y₀ group which can be taken by Y_(a) andY_(a0), of the present compounds (I) and (II), the “5 to 12-memberedhydrocarbon ring which is substituted with a carbonyl group or athiocarbonyl group and, further, may be substituted with an oxy group, athio group, a —NR₁— group (R₁ is as defined above), a sulfinyl group ora sulfonyl group” represents a 5 to 12-membered hydrocarbon ring inwhich one or plural of carbon atoms are substituted with a carbonylgroup or a thiocarbonyl group and, further, one or plural of carbonatoms may be substituted with single or the same or different pluralgroups selected from an oxy group, a thio group, a —NR₁-group (R₁ is asdefined above), a sulfinyl group or a sulfonyl group.

In (e₀) of the substituent Y₀ group which can be taken by Y_(a) andY_(a0), of the present compounds (I) and (II), the “5 to 12-memberedhydrocarbon ring optionally substituted with a carbonyl group, athiocarbonyl group, an oxy group, a thio group, a —NR₁-group (R₁ is asdefined above), a sulfinyl group or a sulfonyl group” represents a 5 to12-membered hydrocarbon ring in which one or plural of carbon atoms maybe substituted with single or the same or different plural groupsselected from a carbonyl group, a thiocarbonyl group, an oxy group, athio group, a —NR₁-group (R₁ is as defined above), a sulfinyl group anda sulfonyl group.

The groups belonging to a X₀ group, a Y₀ group and a Z₀ group which canbe taken by Y_(a) of the present compound (I) will be exemplified in thefollowing Table X, Table Y and Table Z, respectively.

The groups belonging to a X₀ group, a Y₀ group and a Z₀ group which canbe taken by Y_(A0) of the present invention (II) are exemplified in thefollowing Table X, Table Y and Table Z, respectively, and Q₀ and T₀ areexemplified in the following Table Q and Table T, respectively.

The groups belonging to a X group, a Y group and a Z group which can betaken by Y_(A) of the present compound (III) are exemplified in thefollowing Table X, Table Y and Table Z, respectively, and Q and T areexemplified in the following Table Q and Table T, respectively.

The groups belonging to the aforementioned X₀ group to Z₀ group and Xgroup to Z group will be exemplified in the following Table X to Table Zand, when geometrical isomerism is possible, all geometrical isomersthereof are meant and, when tautomerism is possible, all tautomersthereof are meant.

The groups belonging to a X₀ group and a X group will be exemplified inTable X.

TABLE X No. Group X-1 —CH₃ X-2 —C₂H₅ X-3 —CF₃ X-4 —CH═CHCH₃ X-5—CH₂CH═CH₂ X-6 —C≡CH X-7 —F X-8 —Cl X-9 —Br X-10 —NO₂ X-11 —CN X-12—OCH₃ X-13 —SCH₃ X-14 —SOC₄H₉ X-15 —SO₂C₄H₉ X-16 —OCHF₂ X-17 —OCF₃ X-18—OCF₂CHF₂ X-19 —SCF₃ X-20 —CH₂OCH₃ X-21 —COCH₃ X-22 —OCOCH₃ X-23 —COOHX-24 —COOCH₃ X-25 —CH═CHCOOH X-26 —N(CH₃)₂ X-27 —NHCOCH₃ X-28 —NHCOOCH₃X-29 —CONH₂ X-30 —CON(CH₃)₂ X-31 —NHCON(CH₃)₂ X-32 —NHC(═NH)NH₂ X-33—NHSO₂CF₃ X-34 —SO₂N(CH₃)₂

The groups belonging to a Y₀ group and a Y group will be exemplified inTable Y.

TABLE Y No. Group Y-1

Y-2

Y-3

Y-4

Y-5

Y-6

Y-7

Y-8

Y-9

Y-10

An A ring fused with a Z₀ group or a Z group will be exemplified inTable Z.

TABLE Z No. Group Z-1

Z-2

Z-3

Z-4

Z-5

Z-6

Z-7

Z-8

Z-9

Z-10

Q_(A0) and Q_(A) will be exemplified in Table Q.

TABLE Q No. Group Q-1 —OH Q-2

Q-3

Q-4

Q-5 —OCOCH₃ Q-6 —OSO₂N(CH₃)₂ Q-7 —NHCH₂CH═CH₂ Q-8 —NHCH₂C≡CH Q-9—NHCH₂CH₂OCH₃ Q-10 —OCH₃ Q-11 —OCH₂CH₂ (c) C₆H₁₁ Q-12 —OCH₂CH═CH₂ Q-13—OCH₂C≡CH Q-14 —OCH₂COOH Q-15 —OCH₂COOCH₃ Q-16 —OCH₂CONH₂ Q-17 —OCH₂CNQ-18 —OCH₂CH₂OH Q-19 —OCH₂CH₂OCH₃ Q-20 —OCH₂CH₂N(CH₃)₂ Q-21 —OCH₂COCH₃Q-22 —OCOC₆H₅ Q-23 —OCH₂C₆H₅ Q-24

Q-25

Q-26

T_(A0) and T_(A) will be exemplified in Table T.

TABLE T No. Group T-1 —H T-2 —CH₃ T-3 —CH₂CH₂ (c) C₆H₁₁ T-4 —CH₂CH═CH₂T-5 —CH₂C≡CH T-6 —CH₂C₆H₅ T-7 —CH₂COOH T-8 —CH₂COOCH₃ T-9 —CH₂CONH₂ T-10—CH₂CN T-11 —CH₂CH₂OH T-12 —CH₂CH₂OCH₃ T-13 —CH₂CH₂N(CH₃)₂ T-14—CH₂COCH₃ T-15 —CH₂CF₃ T-16 —Ph T-17

Examples of the present compound (I) include the compound wherein Q_(α)is a hydroxy group, a (b)-group ((b₀) is as defined above) or anA₉′-O-group (A₉′ is as defined above) and, at the same time, K_(a) is ahydrogen atom and L_(a) is a methyl group, or K_(a) and L_(a) form a1,3-butadienylene group.

Examples of the present compound (II) include the compound whereinQ_(A0) is a hydroxy group, a (b₀)-group ((b₀) is as defined above) or an(A₉′-O-group (A₉′ is as defined above) and, at the same time, K_(A0) isa hydrogen atom and L_(A0) is a methyl group, or K_(A0) and L_(A0) forma 1,3-butadienylene group.

Examples of the present compound (III) include the compound whereinQ_(A) is a hydroxy group, a (b)-group ((b) is as defined above) or anQ₉′-O-group (A₉′ is as defined above) and, at the same time, K_(A) is ahydrogen atom and L_(A) is a methyl group, or K_(A) and L_(A) form a1,3-butadienylene group.

Examples of the present compound (IV) include the compound wherein Q_(A)is a hydroxy group, a (b)-group ((b) is as defined above) or anA₉′-O-group (A₉′ is as defined above) and, at the same time, K_(a) is ahydrogen atom and L_(a) is a methyl group.

Examples of the present compound (X) include the compound wherein Q_(A)is a hydroxy group, a (b)-group ((b) is as defined above) or anA₉′-O-group (A₉′ is as defined above) and, at the same time, r is 0.

Examples of the present compound (XV) include the compound wherein Q_(A)is a hydroxy group, a (b)-group ((b) is as defined above) or anA₉′-O-group (A₉′ is as defined above) and, at the same time, K_(a) is ahydrogen atom and L_(a) is a methyl group.

Examples of the present compound (XIX) include the case where Q_(A) is ahydroxy group, a (b)-group ((b) is as defined above) or an A₉′-O-group(A₉′ is as defined above) and, at the same time, r is 0.

Some of the present compounds are described in documents such asTetrahedron (1973), 29, 1083, WO 01/79187, Zhurnal PrikladnoiSpektroskopii (1967), 7,638), Khimiya Geterotsiklicheskikh Soedinenii(1967), 4, 682, Chemical Papers (1997), 51, 33 and SyntheticCommunications (2000), 30, 2735, and is known. However, in thesepublications, there is no description about the effect of suppressingtranscription of I type collagen gene in a tissue, in its turn, theeffect of suppressing an accumulated amount of collagen.

The present compounds (V), (VI), (XI), (XII), (XVI) and (XX) are novelcompounds. Although WO 97/35565, JP09227547, WO 00/20371, JP2002371078,WO 01/79187 and WO 92/18483 disclose compounds having a certainconceptional skeleton, there is no specific description of a compoundhaving a similar structure as that of the present compound. In addition,in the publications, there is no description regarding the effect ofsuppressing transcription of I type collagen gene in a tissue, in itsturn, the effect of suppressing an accumulated amount of collagen.

The present compound (I) can be produced by reacting a compoundrepresented by the formula (α) (wherein A, Y_(a) and q are as definedabove) and a compound represented by the formula (α′) (wherein Q_(a),W_(a), K_(a) and L_(a) are as defined above) (see Russian J. GeneralChem. (2001), 71, 1257, Indian J. Chem. (1974), 12, 956 and JP50046666).

The present compound (II) can be produced by reacting a compoundrepresented by the formula (A0) (wherein A, Y_(A0) and q are as definedabove) and a compound represented by the formula (A₀′) (wherein Q_(A0),W_(A0), K_(A0) and L_(A0) are as defined above), as described above.

Among the present compounds, a cinnamoyl compound represented by theformula (II-1):

[wherein A, Y_(A0), q, K_(A0) and L_(A0) are as defined above, rrepresents an A₉′-group (A₉′ is as defined above), W_(A0)′ represents anoxygen atom or a —NT_(A)′-group {T_(A)′ represents an A₉′-group (A₉′ isas defined above), a D₅-R₄-group (D₅ and R₄ are as defined above) or aM_(c)-group (M_(c) is as defined above)}]

-   can be produced by reacting a cinnamoyl compound represented by the    formula (II-2):

[wherein A, Y_(A0), q, K_(A0), L_(A0) and W_(A0)′ are as defined above](hereinafter, referred to as the present intermediate (II-2) in somecases) with a compound represented by the formula (II-3):r-V  (II-3)[r is as defined above, and V represents a leaving group.]

Examples of the reaction method include a method wherein the presentintermediate (II-2) is reacted with a compound (II-3) in the presence ofa base.

The reaction of the present intermediate (II-2) and a compound (II-3) inthe presence of a base is performed usually in a solvent. Examples ofthe solvent used in the reaction include acid amides such asN,N-dimethylformamide, N,N-dimethylacetamide and the like, sulfoxidessuch as dimethyl sulfoxide and the like, phosphoric acid amide compoundssuch as hexamethylphosphoramide and the like, and ketones such asacetone, methyl ethyl ketone and the like.

Examples of the base used in the reaction include alkali metalhydroxides such as sodium hydroxide, potassium hydroxide and the like,and carbonates of an alkali metal such as sodium carbonate, potassiumcarbonate and the like.

Examples of the compound (II-3) include alkylsulfonic acid esters suchas methyl methanesulfonate and the like, arylsulfonic acid esters suchas p-toluenesulfonic acid methyl ester, p-toluenesulfonic acid2-methoxyethyl ester and the like, sulfate esters such as dimethylsulfate and the like, and halides such as methyl iodide,2-chloroethyldimethylamine, allyl bromide, propargyl bromide, methylbromoacetate, bromoacetonitrile, 2-bromoethanol, benzyl bromide,bromoacetone and the like.

The amount of the reagent used in the reaction is such a ratio that abase is usually 1 mole to 2 moles, and a compound (II-3) is usually 1mole to 2 moles per 1 mole of the present intermediate (II-2).

The reaction temperature is usually in a range of 0° C. to 100° C., anda reaction time is usually in a range of 1 hour to 20 hours.

After completion of the reaction, the reaction mixture is extracted withan organic solvent, and the organic layer is subjected to apost-treatment procedure such as drying, concentration and the like,thereby, a cinnamoyl compound (II-1) can be isolated. The isolatedcinnamoyl compound (II-1) can be also further purified bychromatography, recrystallization or the like.

The present intermediate (VI) can be produced by reacting a compoundrepresented by the formula (VI-1) (wherein A, X_(c), Y_(c), p and q areas defined above) and a compound represented by the formula (VI-2)(wherein K_(a) and L_(a) are as defined above) as in the reaction of thecompound (A0) and the compound (A0′).

The present intermediate (XII) can be produced by reacting a compoundrepresented by the formula (XII-1) (wherein A, X_(e), Y_(e), p and q areas defined above) and a compound represented by the formula (XII-2)(wherein M_(a)′ and r are as defined above) as in the reaction of acompound (A0) and a compound (A0′).

Among the present compounds, a 2H-pyran-2-one compound represented bythe formula (VI-3) can be produced by reacting the present intermediate(VI) and the compound (II-3). The reaction can be performed as in thereaction of the present intermediate (II-2) and the compound (II-3).

Among the present compounds, a 2H-1-benzopyran-3-one compoundrepresented by the formula (XII-3) can be produced by reacting thepresent intermediate (XII) and the compound (II-3). The reaction can beperformed as in the reaction of the present intermediate (II-2) and thecompound (II-3).

The present intermediates (VI) and (XII) are novel compounds. AlthoughWO 97/35565, JP09227547, WO 00/20371, JP2002371078, WO 01/79187 and WO92/18483 disclose compounds having a certain conceptional skeleton,there is no specific description of a compound having a similarstructure as that of the present intermediates (VI) and (XII).

Among the present intermediate (II-2), the present intermediate (II-2a)represented by compound numbers (1a-1) to (1a-12) will be exemplified inTable 1a.

TABLE 1a The present intermediate (II-2a) (II-2a)

Compound No. (Y_(A0))_(q) (1a-1) 3-CH═CHCH₃ (1a-2) 3-C≡CH (1a-3)3-CON(CH₃)₂ (1a-4) 3-CH₃, 4-OCH₃ (1a-5) 3-CF₃, 4-Cl (1a-6) 3-Cl, 4-OCF₃(1a-7) 3-F, 4,5-(OCH₃)₂ (1a-8) 3-COOCH₃         Compound No.

(1a-9)

(1a-10)

(1a-11)

(1a-12)

Among the present intermediate (II-2), the present intermediate (II-2b)represented by a compound number (1b-1) to (1b-4) will be exemplified inTable 1b.

TABLE 1b The present intermediate (II-2b) (II-2b)

Com- pound No. The present intermediate (II-2b) (1b-1)

(1b-2)

(1b-3)

(1b-4)

Among the present intermediate (II-2), the present intermediate (II-2c)represented by a compound number (1c-1) to (1c-12) will be exemplifiedin Table 1c.

TABLE 1c The present intermediate (II-2c) (II-2c)

Compound No. (Y_(A0))_(q) (1c-1) 3-CH═CHCH₃ (1c-2) 3-C≡CH (1c-3)3-CON(CH₃)₂ (1c-4) 3-CH₃, 4-OCH₃ (1c-5) 3-CF₃, 4-Cl (1c-6) 3-Cl, 4-OCF₃(1c-7) 3-F, 4,5-(OCH₃)₂ (1c-8) 3-COOCH₃         Compound No.

(1c-9)

(1c-10)

(1c-11)

(1c-12)

Among the present compound (II), the present compound (IIa) representedby a compound number (2a-1) to (2a-28) will be exemplified in Table 2a.

TABLE 2a The present compound (IIa) (IIa)

Compound No. (Y_(AO))_(q) r (2a-1) 3-CH═CHCH₃ CH₃ (2a-2) 3-C≡CH C₂H₅(2a-3) 4-SCH₃ CH₃ (2a-4) 4-S(O)CH₃ CH₃ (2a-5) 4-S(O)₂CH₃ CH₃ (2a-6) 3-CNCH₃ (2a-7) 4-COOH CH₂CH═CH₂ (2a-8) 4-COOCH₃ CH₃ (2a-9) 4-N(CH₃)₂ CH₃(2a-10) 3-NHCOCH₃ CH₂C≡CH (2a-11) 3-NHCON(CH₃)₂ CH₃ (2a-12) 3-CONH₂ CH₃(2a-13) 3-CON(CH₃)₂ CH₃ (2a-14) 3, 4-Cl₂ CH₃ (2a-15) 3-CH₃, 4-OCH₃ CH₃(2a-16) 3-CF₃, 4-Cl CH₃ (2a-17) 3-Cl, 4-OCF₃ CH₃ (2a-18) 3-F,4,5-(OCH₃)₂ CH₃ (2a-19) 3-COOCH₃ CH₃         Compound No.

        r (2a-20)

CH₃ (2a-21)

CH₃ (2a-22)

CH₃ (2a-23)

CH₃ (2a-24) 3-CH₃ CH₂CH₂OCH₃ (2a-25) 3-CH₃ CH₂COOCH₃ (2a-26) 3-CH₃CH₂CH₂CH₂COCH₃ (2a-27) 3-CH₃ CH₂CH₂OH (2a-28) 3-CH₃ CH₂CH₂S(O)₂CH₃

Among the present compound (II), the present compound (IIb) representedby a compound number (2b-1) to (2b-3) will be exemplified in Table 2b.

TABLE 2b The present compound (IIb) (IIb)

Compound No. The present compound (IIb) (2b-1)

(2b-2)

(2b-3)

Among the present compound (II), the present compound (IIc) representedby a compound number (2c-1) to (2c-23) will be exemplified in Table 2c.

TABLE 2c The present compound (IIc) (IIc)

Com- pound No. (Y_(A0))_(q) r (2c-1) 3-CH═CHCH₃ CH₃ (2c-2) 3-C≡CH C₂H₅(2c-3) 4-SCH₃ CH₃ (2c-4) 4-S(O)CH₃ CH₃ (2c-5) 4-S(O)₂CH₃ CH₃ (2c-6) 3-CNCH₃ (2c-7) 4-COOH CH₂CH═CH₂ (2c-8) 4-COOCH₃ CH₃ (2c-9) 4-N(CH₃)₂ CH₃(2c-10) 3-NHCOCH₃ CH₂C≡CH (2c-11) 3-NHCON(CH₃)₂ CH₃ (2c-12) 3-CONH₂ CH₃(2c-13) 3-CON(CH₃)₂ CH₃ (2c-14) 3, 4-Cl₂ CH₃ (2c-15) 3-CH₃, 4-OCH₃ CH₃(2c-16) 3-CF₃, 4-Cl CH₃ (2c-17) 3-Cl, 4-OCF₃ CH₃ (2c-18) 3-F,4,5-(OCH₃)₂ CH₃ (2c-19) 3-COOCH₃ CH₃       Com- pound No.

        r (2c-20)

CH₃ (2c-21)

CH₃ (2c-22)

CH₃ (2c-23)

CH₃

Among the present compound (II), the present compound (IIa′) representedby a compound number (3a-1) to (3a-40) will be exemplified in Table 3a.

TABLE 3a The present compound (IIa′) (IIa′)

Compound No. (Y_(A0))_(q) r r′ (3a-1) H H H (3a-2) H H CH₃ (3a-3) H CH₃CH₃ (3a-4) 3-Cl H H (3a-5) 3-CH₃ H H (3a-6) 4-CF₃ H H (3a-7) 3-CH₂OCH₃ HH (3a-8) 3-CH═CHCH₃ H H (3a-9) 3-C≡CH H H (3a-10) 3-OC₂H₅ H H (3a-11)4-SCH₃ H H (3a-12) 4-S(O)CH₃ H H (3a-13) 4-S(O)₂CH₃ H H (3a-14) 4-NO₂ HH (3a-15) 3-CN H H (3a-16) 4-COOH H H (3a-17) 4-COOCH₃ H H (3a-18)4-N(CH₃)₂ H H (3a-19) 3-NHCOCH₃ H H (3a-20) 3-NHCON(CH₃)₂ H H (3a-21)3-CONH₂ H H (3a-22) 3-CON(CH₃)₂ H H (3a-23) 3-OCHF₂ H H (3a-24) 4-OCF₃ HH (3a-25) 4-OCF₂CHF₂ H H (3a-26) 2-SCF₃ H H (3a-27) 3,4-Cl₂ H H (3a-28)2,4-(OCH₃)₂ H H (3a-29) 3-CH₃, 4-OCH₃ H H (3a-30) 3-OC₂H₅, 4-OH H H(3a-31) 3-CF₃, 4-Cl H H (3a-32) 3-Cl, 4-OCF₃ H H (3a-33) 3-F,4,5-(OCH₃)₂ H H (3a-34) 3-COOCH₃ H CH₃         Compound No.

        r         r′ (3a-35)

H CH₃ (3a-36)

H CH₃ (3a-37)

H H (3a-38)

H CH₃ (3a-39)

H H (3a-40)

H CH₃

Among the present compound (II), the present compound (IIb′) representedby a compound number (3b-1) to (3b-3) will be exemplified in Table 3b.

TABLE 3b The present compound (IIb′) (IIb′)

Compound No. The present compound (IIb′) (3b-1)

(3b-2)

(3b-3)

Among the present compound (II), the present compound (IIc′) representedby a compound number (3c-1) to (3c-40) will be exemplified in Table 3c.

TABLE 3c The present compound (IIc′) (IIc′)

Compound No. (Y_(A0))_(q) r r′ (3c-1) H H H (3c-2) H H CH₃ (3c-3) H CH₃CH₃ (3c-4) 3-Cl H H (3c-5) 3-CH₃ H H (3c-6) 4-CF₃ H H (3c-7) 3-CH₂OCH₃ HH (3c-8) 3-CH═CHCH₃ H H (3c-9) 3-C≡CH H H (3c-10) 3-OC₂H₅ H H (3c-11)4-SCH₃ H H (3c-12) 4-S(O)CH₃ H H (3c-13) 4-S(O)₂CH₃ H H (3c-14) 4-NO₂ HH (3c-15) 3-CN H H (3c-16) 4-COOH H H (3c-17) 4-COOCH₃ H H (3c-18)4-N(CH₃)₂ H H (3c-19) 3-NHCOCH₃ H H (3c-20) 3-NHCON(CH₃)₂ H H (3c-21)3-CONH₂ H H (3c-22) 3-CON(CH₃)₂ H H (3c-23) 3-OCHF₂ H H (3c-24) 4-OCF₃ HH (3c-25) 3-OCF₂CHF₂ H H (3c-26) 2-SCF₃ H H (3c-27) 3,4-Cl₂ H H (3c-28)2,4-(OCH₃)₂ H H (3c-29) 3-CH₃, 4-OCH₃ H H (3c-30) 3-OC₂H₅, 44-OH H H(3c-31) 3-CF₃, 4-Cl H H (3c-32) 3-Cl, 4-OCF₃ H H (3c-33) 3-F,4,5-(OCH₃)₂ H H (3c-34) 3-COOCH₃ H CH₃         Compound No.

        r         r′ (3c-35)

H CH₃ (3c-36)

H CH₃ (3c-37)

H H (3c-38)

H CH₃ (3c-39)

H H (3c-40)

H CH₃

The present compound has the ability to suppress transcription of a TypeI collagen gene. The ability is important in improving tissue fibrosisbecause it decreases expression of a Type I collagen gene to induce areduction in accumulation of collagen. Therefore, the present compoundcan be utilized as an active ingredient of a composition (medicament,cosmetic, food additive etc.) which can improve tissue fibrosis bydecreasing expression of a Type I collagen gene to induce a reduction inaccumulation of collagen.

A disease to which the transcription-suppressing composition of thepresent invention and the fibrosis-improving composition of the presentinvention can be applied includes, for example, a disease in whichexcessive accumulation of collagen causes fibrosis and then sclerosis oftissues, resulting in decreased function, cicatrization and the like inthe tissues such as organs (i.e. fibrosing disease etc.). Specifically,the disease includes diseases and disorders such as hepatic cirrhosis,interstitial pulmonary disease, chronic renal failure (or diseaseresulting in chronic renal failure), hyperplasia scar afterinflammation, postoperative scars or burn scars, scleroderma,arteriosclerosis, hypertension and the like. Incidentally, as an exampleof hepatic cirrhosis, it has been already known that C type or B typehepatitis virus induces chronic inflammation and then increasedproduction of TGF-β, and thereby, hepatic fibrosis (particularly,accumulation of type I and type III collagen) is induced to causehepatic cirrhosis (e.g. see Clin. Liver Dis., 7, 195-210 (2003)). As anexample of interstitial pulmonary disease, it has been thought thatpneumonia caused by mites, viruses, tubercle bacilli or the like inducesincreased production of TGF-β and then pulmonary fibrosis, and therebyinterstitial pulmonary disease is caused. For chronic renal failure suchas diabetic nephropathy and IgA nephropathy, it has been alreadysuggested that diabetic nephropathy is caused by increased level ofTGF-β in renal glomeruli due to hyperglycemia and thereby induction ofrenal fibrosis (particularly accumulation of Type I and Type IVcollagen), and IgA nephropathy is caused by induction of nephritis dueto accumulation of IgA in renal glomeruli followed by increased level ofTGF-β, and thereby induction of renal fibrosis (particularlyaccumulation of Type I and Type IV collagen) (e.g. see Am. J. Physiol.Renal Phsiol., 278, F830-F838 (2000), Kidney Int. 64.149-159 (2003)). Adb/db mouse, a diabetic nephropathy model animal, develops hyperglycemiaby overeating because it has a mutation in a leptin receptor forsuppressing ingestion, and then spontaneously develops diabetes. In thedb/db mouse, the blood glucose concentration is about 4 times higherthan a normal mouse, and fibrosis of renal glomeruli and increased levelof TGF-β are found (e.g. see Am. J. Pathol., 158, 1653-1663 (2001)). Ananti-Thy-1 rat, an IgA nephropathy model animal, is produced byadministering an anti-Thy-1 antibody to a normal rat to artificiallycause renal fibrosis. It has been shown that renal fibrosis issuppressed by administering an anti-TGF-β receptor antibody to the modelanimal (e.g. see Kidney Int., 60, 1745-1755 (2001)). Although the causeof scleroderma is unknown, it has been found that skin fibrosis isimproved by administering a TGF-β inhibitor to a Tsk mouse, which is amodel animal therefor (e.g. see J. Invest. Dermatol., 118.461-470(2001)). Thus, a compound which suppresses the activity of TGF-β can beutilized as an active ingredient of a composition (medicament, cosmetic,food additive etc.) for inhibiting the collagen synthesis-promotingactivity of TGF-β to suppress tissue fibrosis and thereby providing afibrosing disease therapeutic effect.

Such transcription-suppressing composition and fibrosis-improvingcomposition of the present invention comprise the present compound andan inert carrier. Such composition usually comprises 0.01% by weight to99.99% by weight of the present compound and 99.99% by weight to 0.01%by weight of an inert carrier. The inert carrier is a pharmaceuticallyacceptable carrier or excipient. The transcription-suppressingcomposition and fibrosis-improving composition of the present inventionmay further comprise pharmaceutical additives, cosmetic additives, foodadditives and the like.

The present compound also inhibits the ability of TGF-β to promotetranscription of a Type I collagen gene, as shown in Example 22 below.That is, the present compound is a TGF-β antagonist having the abilityto suppress the activity of TGF-β. Therefore, the present compound canbe also utilized as an active ingredient of a composition forsuppressing the activity of TGF-β. It has been known that TGF-β has theability to promote transition from a growth phase (hereinafter, alsoreferred to as hair growth phase in some cases) to a regression phase(hereinafter, also referred to as a hair regression phase in some cases)in the hair life cycle [J. Invest. Dermatol., 111, 948-954 (1998), FASEBJ., 16, 1967-1969 (2002)]. Further, it has been reported that ananti-TGF-β antibody, Fetuin, which is a TGF-β inhibitor, and the likeantagonize the suppressing-activity of TGF-β on hair extension andexhibit a promoting-effect on hair extension [J. Invest. Dermaton., 118,993-997 (2002), JP-A 2000-342296]. Therefore, the present compound (anda TGF-β activity-suppressing composition containing the present compoundas an active ingredient) may be utilized for inhibiting a promotingeffect of TGF-β on transition to a hair regression phase to induceextension of a hair growth phase and thereby providing a hair-growingeffect.

Such TGF-β suppressing composition and hair-growing composition of thepresent invention comprise the present compound and an inert carrier.Such composition usually comprises 0.01% by weight to 99.99% by weightof the present compound and 99.99% by weight to 0.01% by weight of aninert carrier. The inert carrier is a pharmaceutically acceptablecarrier or excipient. The TGF-β suppressing composition and hair-growingcomposition of the present invention may further comprise pharmaceuticaladditives, cosmetic additives, food additives and the like.

A pharmaceutically acceptable carrier, excipient, pharmaceuticaladditive, food additive, cosmetic additive, a medicament additive, andthe like contained in the above-described composition can beappropriately selected depending on the specific use thereof. Inaddition, the composition may be in a form of various solids, liquidsand the like depending on the specific use thereof.

For example, when the present compound is used as an active ingredientof a medicament, specific examples of the medicament include oralpreparations such as powders, fine granules, granules, tablets, syrups,capsules, suspensions, emulsions, extracts and pills; and parenteralpreparations such as injections, transdermal absorbing agents such asexternal liquids and ointments, suppositories and local preparations.

Oral preparations can be prepared using carriers or excipients, andpharmaceutical additives such as binders, disintegrants, surfactants,lubricants, glidants, diluents, preservatives, coloring agents, flavors,stabilizers, humectants, antiseptics, antioxidants and the like, forexample, gelatin, sodium alginate, starch, corn starch, white sugar,lactose, glucose, mannit, carboxymethylcellulose, dextrin,polyvinylpyrrolidone, crystalline cellulose, soybean lecithin, sucrose,fatty acid ester, talc, magnesium stearate, polyethylene glycol,magnesium silicate, anhydrous silicic acid and the like, according to aconventional method.

A dose of the oral preparation varies depending on the age, sex andweight of a mammal to be administered, the severity of disease, the kindand dosage form of the composition of the present invention, and thelike. Usually, in the case of oral administration, about 1 mg to about 2g per day, preferably about 5 mg to about 1 g per day of the activeingredient may be administered to an adult human. The daily dose may bealso administered at one time or in several divided doses.

Among parenteral preparations, an injection can be prepared using suchas a water-soluble solvent such as physiological saline or sterilizedwater Ringer solution, a water-insoluble solvent such as vegetable oilor fatty acid ester, an isotonic agent such as glucose or sodiumchloride, pharmaceutical additives such as a solubilizer, a stabilizer,an antiseptic, a suspending agent and an emulsifying agent, and thelike, according to a conventional method. A transdermal absorbing agentsuch as external liquid or a gel-like ointment, a suppository for rectaladministration and the like can be also prepared according to aconventional method. For administering such parenteral preparations,they may be administered by injection (subcutaneously, intravenouslyetc.), transdermally, or rectally. A local preparation can be prepared,for example, by incorporating the present compound into a pellet of asustained-release polymer such as ethylene vinyl acetate polymer. Thepellet may be surgically transplanted into a tissue to be treated.

A dose of the parenteral preparation varies depending on the age, sexand weight of a mammal to be administered, the severity of disease, thekind and dosage form of the composition of the present invention, andthe like. Usually, in the case of administration by injection, about 0.1mg to about 500 mg of the active ingredient may be administered to anadult human. The daily dose may be also administered at one time or inseveral divided doses.

When the present compound is used by adding to cosmetics, specificexamples of the form of a cosmetic with comprises the present compoundinclude liquid, emulsion, cream, lotion, ointment, gel, aerosol, mousseand the like. Lotion can be prepared using cosmetic additives such as asuspending agent, an emulsifier, a preservative and the like, accordingto a conventional method.

A dose of the cosmetic varies depending on the age, sex and weight of amammal to be administered, the severity of disease, the kind and dosageform of the composition of the present invention, and the like. Usually,about 0.01 mg to about 50 mg of the active ingredient may beadministered to an adult human. The daily dose may be also administeredat one time or in several divided doses.

When the present compound is used as a food additive, specific examplesof the form of a food which comprises the additive include powder, atablet, a beverage, an edible gel or a mixed liquid of the gel andsyrup, for example, general beverage and food and luxury food andbeverage such as seasonings, Japanese confectioneries, westernconfectioneries, ice confectioneries, beverage, spreads, pastes,pickles, bottled or canned products, processed domestic animal meats,processed fish meats or marine product, processed dairy or egg products,processed vegetables, processed fruits, processed cereals and the like.Alternatively, the present compound can be also added to feeds orprovenders for rearing animals such as livestocks, poultry, honey bee,silkworm, fish and the like.

A dose of the food varies depending on the age, sex and weight of amammal to be administered, the severity of disease, the kind and dosageform of the composition of the present invention, and the like. Usually,about 0.1 mg to about 500 mg of the active ingredient may beadministered to an adult human. The daily dose may be also administeredat one time or in several divided doses.

EXAMPLES

The present invention will be further specifically explained below byway of Examples.

Example 1 Synthesis of the Present Intermediate (II-2a) [Compound No.(1a-6)]

A mixture of 1.85 g of 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one, 2.25g of 3-chloro-4-(trifluoromethoxy)benzaldehyde, 20 ml of chloroform and0.7 ml of piperidine was heated under refluxing for 4 hours. Aftercooling to room temperature, the reaction mixture was concentrated underreduced pressure, and the residue was subjected to columnchromatography. Resulting crystals were washed with 40 ml of t-butylmethyl ether to obtain 0.40 g of4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one[Compound No. (1a-6]) as a yellow crystal.

¹H-NMR (300 MHz, CDCl₃) δ (ppm): 2.31 (s, 3H), 5.70 (s, 1H), 7.38 (d,1H), 7.61 (d, 1H), 7.78 (s, 1H), 7.80 (d, 1H, J=15.0 Hz), 8.27 (d, 1H,J=15.0 Hz)

Example 2 Synthesis of the Present Intermediate (II-2a) [Compound No.(1a-9)]

According to the same manner as that of Example 1 except that 2.57 g of3-([1,3]dioxolan-2-yl)benzaldehyde was used in place of3-chloro-4-(trifluoromethoxy)benzaldehyde, 0.38 g of4-hydroxy-3-[3-[3-([1,3]dioxolan-2-yl)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one[Compound No. (1a-9)] was obtained as a pale yellow crystal.

¹H-NMR (400 MHz, CDCl₃) δ (ppm): 2.29 (s, 3H), 4.04-4.17 (m, 4H), 5.84(s, 1H), 5.96 (s, 1H), 7.44 (t, 1H, J=7.7 Hz), 7.54 (d, 1H, J=7.6 Hz),7.70 (d, 1H, J=7.8 Hz), 7.78 (s, 1H), 7.97 (d, 1H, J=15.9 Hz), 8.32 (d,1H, J=15.9 Hz)

Example 3 Synthesis of the Present Intermediate (II-2a) [Compound No.(1a-10)]

According to the same manner as that of Example 1 except that 4.97 g of2,3-dihydro-1,4-benzodioxin-6-carbaldehyde was used in place of3-chloro-4-(trifluoromethoxy)benzaldehyde, 0.50 g of4-hydroxy-3-[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one[Compound No. (1a-10)] was obtained as a pale yellow crystal.

¹H-NMR (300 MHz, CDCl₃) δ (ppm): 2.27 (s, 3H), 4.28-4.31 (m, 4H), 5.94(s, 1H), 6.90 (d, 1H, J=8.1 Hz), 7.21-7.24 (m, 2H), 7.88 (d, 1H, J=15.6Hz), 8.17 (d, 1H, J=15.6 Hz), 12.19 (s, 1H)

Example 4 Synthesis of the Present Intermediate (II-2b) [Compound No.(1b-1)]

According to the same manner as that of Example 1 except thatn-tolualdehyde was used in place of3-chloro-4-(trifluoromethoxy)benzaldehyde, and3-acetyl-5-bromo-4-hydroxy-6-methyl-2H-pyran-2-one was used in place of3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one,5-bromo-4-hydroxy-3-[3-(3-methylphenyl)-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one[Compound No. (1b-1)] was obtained as a pale yellow crystal.

¹H-NMR (400 MHz, CDCl₃) δ (ppm): 2.40 (s, 3H), 2.50 (s, 3H), 7.25-7.34(m, 2H), 7.49-7.51 (m, 2H), 8.05 (d, 1H, J=15.9 Hz), 8.30 (d, 1H, J=15.9Hz)

Example 5 Synthesis of the Present Intermediate (II-2b) [Compound No.(1b-4)]

According to the same manner as that of Example 1 except that3-acetyl-4-hydroxy-6-phenyl-2H-pyran-2-one was used in place of3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one,4-hydroxy-3-[3-(3-methylphenyl)-1-oxo-2-propenyl]-6-phenyl-2H-pyran-2-one[Compound No. (1b-4)] was obtained.

¹H-NMR (400 MHz, CDCl₃) δ (ppm): 2.40 (s, 3H), 6.59 (s, 1H), 7.22-7.28(1H), 7.32 (t, 1H, J=7.6 Hz), 7.48-7.58 (m, 5H), 7.86-7.93 (m, 2H), 7.97(d, 1H, J=15.6 Hz), 8.35 (d, 1H, J=15.8 Hz), 12.06 (s, 1H)

Example 6 Synthesis of the Present Intermediate (II-2c) [Compound No.(1c-6)]

A mixture of 2.25 g of 3-acetyl-4-hydroxy-2H-1-benzopyran-2-one, 2.25 gof 3-chloro-4-(trifluoromethoxy)benzaldehyde, 20 ml of chloroform and0.7 ml of piperidine was heated under refluxing for 2 hours and 30minutes. After cooled to room temperature, the reaction mixture wasconcentrated under reduced pressure, and the residue was subjected tocolumn chromatography. Resulting crystals were washed with 40 ml oft-butyl methyl ether to obtain 1.49 g of4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one[Compound No. (1c-6)] was obtained as a yellow crystal.

¹H-NMR (270 MHz, CDCl₃) δ (ppm): 7.30-7.40 (3H), 7.63 (dd, 1H, J=2.2,8.6 Hz), 7.72 (t, 1H, J=7.8 Hz), 7.81 (d, 1H, J=2.2 Hz), 7.91 (d, 1H,J=15.4 Hz), 8.10 (dd, 1H, J=1.6, 7.6 Hz), 8.41 (d, 1H, J=15.9 Hz), 18.64(s, 1H)

Example 7 Synthesis of the Present Compound (IIa) [Compound No. (2a-17)]

In 4 ml of hexamethylphosphoramide was dissolved 0.33 g of4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one,to this solution was added 50 mg of sodium hydride (60% oily), and themixture was stirred at room temperature for 30 minutes. Then, 0.2 ml ofdimethyl sulfate was added, and the mixture was stirred at 65° C. for 1hour, and at room temperature overnight. Thereafter, the reactionmixture was added to ice water, and this was extracted with ethylacetate. The organic layer was washed with an aqueous saturated sodiumchloride solution, dried with anhydrous magnesium sulfate, andconcentrated. The residue was subjected to silica gel columnchromatography to obtain 0.13 g of4-methoxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran[Compound No. (2a-17)] as a pale yellow crystal.

¹H-NMR (270 MHz, CDCl₃) δ (ppm): 2.31 (s, 3H), 3.95 (s, 3H), 5.99 (s,1H), 7.16 (d, 1H, J=15.9 Hz), 7.32 (d, 1H, J=7.6 Hz), 7.47 (d, 1H, J=6.5Hz), 7.53 (d, 1H, J=15.9 Hz), 7.68 (d, 1H, J=1.9 Hz)

Example 8 Synthesis of the Present Compound (IIa) [Compound No. (2a-20)]

According to the same manner as that of Example 7 except that 0.35 g of4-hydroxy-3-[3-[3-([1,3]dioxolan-2-yl)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-onewas used in place of4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one,0.18 g of4-methoxy-3-[3-[3-([1,3]dioxolan-2-yl)phenyl]-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one[Compound No. (2a-20)] was obtained as a pale yellow oil.

¹H-NMR (400 MHz, CDCl₃) δ (ppm): 2.35 (s, 3H), 3.93 (s, 3H), 4.03-4.18(m, 4H), 5.82 (s, 1H), 6.12 (s, 1H), 7.15 (d, 1H, J=16.0 Hz), 7.39 (t,1H, J=7.7 Hz), 7.49 (d, 1H, J=7.6 Hz), 7.57 (d, 1H, J=7.6 Hz), 7.62 (d,1H, J=16.0 Hz), 7.68 (s, 1H)

Example 9 Synthesis of the Present Compound (II-a) [Compound No.(2a-24)]

To a mixture of 0.81 g of4-hydroxy-3-[3-(3-methylphenyl)-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one,10 ml of tetrahydrofuran, 0.25 ml of 2-methoxyethanol, and 0.87 g oftriphenylphosphine was added dropwise a solution of 0.57 g of diethylazodicarboxylate in 6 ml of tetrahydrofuran, and this was stirred atroom temperature overnight. The solvent was distilled off under reducedpressure, and the resulting residue was subjected to silica gel columnchromatography to obtain 389 mg of4-(2-methoxyethoxy)-3-[3-(3-methylphenyl)-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one[Compound No. (2a-24)] as a yellow oil.

¹H-NMR (400 MHz, CDCl₃) δ (ppm): 2.32 (s, 3H), 2.36 (s, 3H), 3.33 (s,3H), 3.66 (t, 2H, J=4.6 Hz), 4.25 (t, 2H, J=4.6 Hz), 6.12 (s, 1H), 7.09(d, 1H, J=15.9 Hz), 7.15-7.40 (4H), 7.56 (d, 1H, J=15.9 Hz)

Example 10 Synthesis of the Present Compound (IIa) [Compound No.(2a-25)]

According to the same manner as that of Example 9 except that 0.25 ml ofmethyl glycolate was used in place of 2-methoxyethanol, 470 mg of4-methoxycarbonylmethoxy-3-[3-(3-methylphenyl)-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one[Compound No. (2a-25)] was obtained.

¹H-NMR (400 MHz, CDCl₃) δ (ppm): 2.30 (s, 3H), 2.35 (s, 3H), 3.79 (s,3H), 4.75 (s, 2H), 5.95 (s, 1H), 7.06 (d, 1H, J=16.2 Hz), 7.20-7.80 (5H)

Example 11 Synthesis of the Present Compound (IIa) [Compound No.(2a-26)]

According to the same manner as that of Example 9 except that 0.34 ml of3-acetyl-1-propanol was used in place of 2-methoxyethanol, 98 mg of4-(3-acetylpropoxy)-3-[3-(3-methylphenyl)-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one[Compound No. (2a-26)] was obtained.

¹H-NMR (400 MHz, CDCl₃) δ (ppm): 1.95-2.05 (m, 2H), 2.07 (s, 3H), 2.33(s, 3H), 2.36 (s, 3H), 2.61 (t, 2H, J=6.6 Hz), 4.15 (t, 2H, J=6.1 Hz),6.12 (s, 1H), 7.09 (d, 1H, J=16.2 Hz), 7.15-7.40(4H), 7.54 (d, 1H,J=16.2 Hz)

Example 12 Synthesis of the Present Compound (IIa) [Compound No.(2a-27)]

According to the same manner as that of Example 9 except that 0.52 ml ofethylene glycol monoacetate was used in place of 2-methoxyethanol, 40 mgof4-(2-hydroxyethoxy)-3-[3-(3-methylphenyl)-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one[Compound No. (2a-27)] was obtained.

¹H-NMR (400 MHz, CDCl₃) δ (ppm): 2.34 (s, 3H), 2.36 (s, 3H), 3.34 (t,2H, J=6.4 Hz), 3.88-3.92 (m, 2H), 4.26 (t, 2H, J=4.6 Hz), 6.09 (s, 1H),7.15-7.45 (m, 5H), 7.64 (d, 1H, J=16.1 Hz)

Example 13 Synthesis of the Present Compound (IIa) [Compound No.(2a-28)]

According to the same manner as that of Example 9 except that 0.32 ml of2-(methylsulfonyl)ethanol was used in place of 2-methoxyethanol, 137 mgof4-(2-methylsulfonylethoxy)-3-[3-(3-methylphenyl)-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one[Compound No. (2a-28)] was obtained.

¹H-NMR (400 MHz, CDCl₃) δ (ppm): 2.38 (s, 6H), 3.05 (s, 3H), 3.42 (t,2H, J=5.6 Hz), 4.56 (t, 2H, J=5.2 Hz), 6.12 (s, 1H), 7.13 (d, 1H, J=16.1Hz), 7.15-7.40 (4H), 7.55 (d, 1H, J=15.9 Hz)

Example 14 Synthesis of the Present Compound (IIc) [Compound No.(2c-17)]

In 15 ml of hexamethylphosphoramide was dissolved 1.37 g of4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]1-oxo-2-propenyl]-2H-1-benzopyran-2-one,to this solution was added 0.17 g of sodium hydride (60% oily), and thiswas stirred at room temperature for 30 minutes. Then, 0.8 ml of dimethylsulfate, and this was stirred at 65° C. for 2 hours. Thereafter, thereaction mixture was added to ice water, and this was extracted withethyl acetate. The organic layer was washed with an aqueous saturatedsodium chloride solution, dried with anhydrous magnesium sulfate, andconcentrated. The residue was washed with t-butyl methyl ether to obtain0.38 g of4-methoxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one[Compound No. (2c-17)] as a pale yellow crystal.

¹H-NMR (270 MHz, CDCl₃) δ (ppm): 3.97 (s, 3H), 7.16 (d, 1H, J=15.9 Hz),7.30-7.40 (2H), 7.48-7.55 (1H), 7.54 (d, 1H, J=15.9 Hz), 7.55-7.65 (2H),7.71 (d, 1H, J=1.9 Hz), 7.92 (dd, 1H, J=1.4, 7.8 Hz)

Example 15 Synthesis of the Present Compound (IIa′) [Compound No.(3a-32)]

A mixture of 0.50 g of 3-acetyl-4-hydroxy-6-methyl-2(1H)-pyridinone,0.74 g of 3-chloro-4-(trifluoromethoxy)benzaldehyde, 6 mg of pyridineand 0.1 ml of piperidine was heated under refluxing for 4 hours. Aftercooled to room temperature, 40 ml of water was added to the reactionmixture, precipitated crystals were filtered, and this was washed withtetrahydrofuran, then with ethyl acetate to obtain 0.41 g of4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone[Compound No. (3a-32)] as a yellow crystal.

¹H-NMR (270 MHz, DMSO-d₆) δ (ppm): 2.22 (s, 3H), 5.90 (s, 1H), 7.60-7.70(2H), 7.76 (d, 1H, J=16.2 Hz), 8.01 (s, 1H), 8.49 (d, 1H, J=15.9 Hz),11.62 (s, 1H), 16.14 (s, 1H)

Example 16 Synthesis of the Present Compound (IIa′) [Compound No.(3a-34)]

In a mixture of 2 ml of pyridine and 0.05 ml of piperidine weredissolved 0.23 g of 3-acetyl-4-hydroxy-1,6-dimethyl-2(1H)-pyridinone and0.23 g of 3-(methoxycarbonyl)benazldehyde, and the solution was heatedunder refluxing for 2 hours. After cooled to room temperature, this wasconcentrated under reduced pressure, and the residue was subjected tosilica gel column chromatography to obtain 0.06 g of4-hydroxy-3-[3-[3-(methoxycarbonyl)phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone[Compound No. (3a-34)] as a yellow crystal.

¹H-NMR (270 MHz, DMSO-d₆) δ (ppm): 2.41 (s, 3H), 3.41 (s, 3H), 3.89 (s,3H), 6.07 (s, 1H), 7.63 (t, 1H, J=7.8 Hz), 7.85 (d, 1H, J=15.8 Hz),7.96-8.03 (m, 2H), 8.25 (s, 1H), 8.54 (d, 1H, J=15.8 Hz), 15.92 (broads,1H)

Example 17 Synthesis of the Present Compound (IIa′) [Compound No.(3a-37)]

To a solution of 2.93 g of 3-[N-(t-butoxycarbonyl)amino]benzaldehyde in20 ml of dimethylformamide was added 0.58 g of sodium hydride (60% oily)under ice-cooling. After stirring at room temperature for 1 hour, asolution of 0.93 ml of 2-bromoethanol in 5 ml of dimethylformamide wasadded dropwise under ice-cooling. After stirring at room temperature for14 hours, the mixture was heated to stir at 115° C. for 6 hours. Ethylacetate was added, and this was washed successively with water and anaqueous saturated sedum chloride solution, dried with anhydrous sodiumsulfate, and concentrated. The residue was subjected to silica gelcolumn chromatography to obtain 0.75 g of oily3-(2-oxo-oxazolidin-3-yl)benzaldehyde.

¹H-NMR (270 MHz, DMSO-d₆) δ (ppm): 4.10-4.16 (m, 2H), 4.44-4.51 (m, 2H),7.61-7.71 (m, 2H), 7.86-7.91 (m, 1H), 8.10-8.12 (m, 1H), 10.03 (s, 1H)

According to the same manner as that of Example 16 except that 0.33 g of3-acetyl-4-hydroxy-6-methyl-2(1H)-pyridinone was used in place of3-acetyl-4-hydroxy-1,6-dimethyl-2(1H)-pyridinone, and 0.30 g of3-(2-oxo-oxazolidin-3-yl)benzaldehyde was used in place of3-(methoxycarbonyl)benzaldehyde, 0.22 g of4-hydroxy-3-[3-[3-(2-oxo-oxazolidin-3-yl)phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone[Compound No. (3a-37)] was obtained as a yellow crystal.

¹H-NMR (300 MHz, DMSO-d₆) δ (ppm): 2.21 (s, 3H), 4.11 (t, 2H, J=7.5 Hz),4.47 (t, 2H, J=7.5 Hz), 5.89 (s, 1H), 7.38-7.53 (m, 2H), 7.65-7.69 (m,1H), 7.81 (d, 1H, J=15.0 Hz), 7.89 (s, 1H), 8.53 (d, 1H, J=15.0 Hz),11.57 (broads, 1H)

Example 18 Synthesis of the Present Compound (IIa′) [Compound No.(3a-38)]

According to the same manner as that of Example 16 except that 0.42 g of3-(2-oxo-oxazolidin-3-yl)benzaldehyde was used in place of3-(methoxycarbonyl)benzaldehyde, 0.25 g of4-hydroxy-3-[3-[3-(2-oxo-oxazolidin-3-yl)phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone[Compound No. (3a-38)] was obtained as a yellow crystal.

¹H-NMR (270 MHz, DMSO-d₆) δ (ppm): 2.41 (s, 3H), 3.40 (s, 3H), 4.09-4.15(m, 2H), 4.44-4.50 (m, 2H), 6.06 (s, 1H), 7.48-7.53 (m, 2H), 7.65-7.69(m, 1H), 7.80 (d, 1H, J=16.1 Hz), 7.89 (s, 1H), 8.50 (d, 1H, J=16.1 Hz),16.03 (broads, 1H)

Example 19 Synthesis of the Present Compound (IIa′) [Compound No.(3a-39)]

According to the same manner as that of Example 16 except that 1.09 g of3-acetyl-4-hydroxy-6-methyl-2(1H)-pyridinone was used in place of3-acetyl-4-hydroxy-1,6-dimethyl-2(1H)-pyridinone, and 1.68 g of3-(2-morpholinoethoxy)benzaldehyde was used in place of3-(methoxycarbonyl)benzaldehyde, 0.27 g of4-hydroxy-3-[3-[3-(2-morpholinoethoxy)phenyl]-1-oxo-2-propenyl]-6-methyl-2(1H)-pyridinone[Compound No. (3a-39)] was obtained as a yellow crystal.

¹H-NMR (270 MHz, DMSO-d₆) δ (ppm): 2.21 (s, 3H), 2.47-2.50 (m, 4H), 2.71(t, 2H, J=5.4 Hz), 3.58 (t, 4H, J=4.6 Hz), 4.14 (t, 2H, J=5.4 Hz), 5.88(s, 1H), 7.05 (d, 1H, J=8.4 Hz), 7.24-7.41 (m, 3H), 7.77 (d, 1H, J=16.2Hz), 8.50 (d, 1H, J=16.2 Hz), 11.56 (s, 1H), 16.42 (s, 1H)

Example 20 Synthesis of the Present Compound (IIa′) [Compound No.(3a-40)]

According to the same manner as that of Example 16 except that 4.87 g of3-(2-morpholinoethoxy)benzaldehyde was used in place of3-(methoxycarbonyl)benzaldehyde, 0.86 g of4-hydroxy-3-[3-[3-(2-morpholinoethoxy)phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone[Compound No. (3a-40)] was obtained as a yellow crystal.

¹H-NMR (300 MHz, DMSO-d₆) δ (ppm): 2.38 (s, 3H), 2.41-2.50 (m, 4H), 2.71(t, 2H, J=5.4 Hz), 3.32 (s, 3H), 3.57-3.60 (m, 4H), 4.14 (t, 2H, J=5.4Hz), 6.06 (s, 1H), 7.03-7.07 (m, 1H), 7.25-7.54 (m, 3H), 7.77 (d, 1H,J=13.5 Hz), 8.46 (d, 1H, J=16.2 Hz)

Example 21 Synthesis of the Present Compound (IIc′) [Compound No.(3c-32)]

A mixture of 0.60 g of 3-acetyl-4-hydroxy-2(1H)-quinolinone, 1.99 g of3-chloro-4-(trifluoromethoxy)benzaldehyde, 10 ml of pyridine and 88 μlof piperidine was heated under refluxing overnight. After cooling toroom temperature, 50 ml of water was added to the reaction mixture, andprecipitated crystals were filtered, and washed with 40 ml oftetrahydrofuran, and 60 ml of hexane to obtain 0.92 g of4-hydroxy-3-[3-[3-chloro-4-(trifluoromethoxy)phenyl]-1-oxo-2-propenyl]-2(1H)-quinolinone[Compound No. (3c-32)] as a yellow crystal.

¹H-NMR (270 MHz, DMSO-d₆) δ (ppm): 7.26 (t, 1H, J=7.8 Hz), 7.32 (d, 1H,J=8.4 Hz), 7.65-7.75 (2H), 7.87 (d, 1H, J=8.4 Hz), 7.87 (d, 1H, J=17.0Hz), 8.03 (d, 1H, J=7.8 Hz), 8.07 (s, 1H), 8.60 (d, 1H, J=15.9 Hz),11.56 (s, 1H), 17.71 (s, 1H)

Example 22 Preparation of a Plasmid Having a Reporter Gene Linked to aTranscription Regulatory Region for a Type I Collagen Gene

1×10⁸ cells of a normal human fetal skin fibroblast (Clontech, catalogueNo. CC-2509) were cultured at 37° C. overnight under 5% CO₂ atmosphere.After the cultured cells were washed with a sodium phosphate buffer(hereinafter, referred to as PBS) twice, 3 ml of PBS was added theretoand the cells were scraped away the wall of a vessel using a cellscraper (Nalgen, catalogue No. 179693). The scraped cells were collectedby centrifugation (1,500 rpm, 4° C., 15 min), and these were suspendedin 20 ml of PBS and centrifuged again. To the resulting precipitateswere added 11 ml of Solution 2 and 4.8 μl of pronase of DNA ExtractionKit (Stratagene, catalogue No. 200600). After shaken at 60° C. for 1hour, the resulting mixture was allowed to stand in ice for 10 minutes.Then, 4 ml of Solution 3 of the kit was added to the mixture. Aftermixed, the mixture was allowed to stand in ice for 5 minutes and thencentrifuged (3,000 rpm, 4° C., 15 min) to recover a supernatant. To therecovered supernatant was added 2 μl of RNase per 1 ml of thesupernatant and the mixture was allowed to stand at 37° C. for 15minutes. To the mixture was added 2-fold volume of ethanol. After mixed,a white thread-like substance (genomic DNA) appeared and the substancewas recovered. The recovered genomic DNA was washed with 70% ethanol andthen air-dried. The air-dried genomic DNA was dissolved in 500 μl of 10mM Tris-HCl, 1 mM EDTA (pH 8.0) (hereinafter, referred to as TE).

The resulting genomic DNA solution (the amount equivalent to 1 μg ofgenomic DNA), each 1 μl (10 μmol/μl) of an oligonucleotide consisting ofthe nucleotide sequence represented by SEQ ID No:1 and anoligonucleotide consisting of the nucleotide sequence represented by SEQID No: 2, 29 μL of distilled water, 5 μl of the buffer attached toTaKaRa LA Taq (TAKARA SHUZO, catalogue No. RR002A), 5 μL of a Mg²⁺solution, 5 μL of a dNTP mixture and 0.5 μl of TaKaRa LA Taq (TAKARASHUZO, catalogue No. RR002A) were mixed. After the resulting mixedsolution was incubated at 94° C. for 5 minutes, the mixed solution wassubjected to 30 cycles, in which one cycle consists of incubation at 94°C. for 1 minute, at 60° C. for 1 minute and then at 72° C. for 1 minute.The mixed solution was electrophoresed on a 2% agarose gel to recoverabout 0.5 kb of a DNA. The recovered DNA was treated withphenol/chloroform and then precipitated with ethanol to recover the DNA.The resulting DNA was dissolved in ultrapure water. To this solutionwere added 2.5 μl of NheI and 2.5 μl of HindIII, and then incubated at37° C. for 3 hours. Then, the solution was electrophoresed on a 2%agarose gel to recover about 3.5 kb of a DNA. The recovered DNA wasprecipitated with ethanol to recover again the DNA (hereinafter,referred to as the collagen promoter DNA).

On the other hand, the vector pGL3 (Promega, catalogue No. E1751) havingthe nucleotide sequence encoding firefly luciferase was digested withNheI and HindIII, and then subjected to agarose gel electrophoresis asdescribed above to recover about 5 kb of a DNA. The recovered DNA wasprecipitated with ethanol to recover the DNA again. To the recovered DNAwere added 44 μl of distilled water, 5 μl of Buffer attached to AlkalinePhosphatase (TAKARA SHUZO, catalogue No. 2120A) and 1 μl of AlkalinePhosphatase (TAKARA SHUZO, catalogue No. 2120A). The mixed solution wasincubated at 65° C. for 30 minutes. Then, the mixed solution was treatedwith phenol/chloroform twice, and precipitated with ethanol to recoverthe DNA (hereinafter referred to as the Luc vector DNA). Then, afterabout 20 ng of the collagen promoter DNA and about 20 ng of the Lucvector DNA were mixed, the same amount of a DNA Ligation kit Ver2 enzymesolution was added and this was incubated overnight at 16° C. To themixed solution was added Escherichia coli 5Hdα (TOYOBO, catalogue No.DNA-903), this was allowed to stand in ice for 30 minutes, and thenincubated at 42° C. for 45 seconds. The resulting Escherichia coli wasseeded on a LB plate containing 50 μg/ml ampicillin sodium (Nacalai,catalogue No. 027-39), and this was allowed to stand at 37° C. for 1day. A single colony appeared and the colony was cultured in 2 ml of aLB medium containing 50 μg/ml ampicillin at 37° C. for 12 hours. Fromthe resulting culture solution, a plasmid DNA was prepared usingAUTOMATIC DNA ISOLATION SYSTEM PI-50 (KURABO). The nucleotide sequenceof the prepared plasmid DNA was analyzed with a DNA sequencer. As aresult, it was confirmed that the plasmid (hereinafter, referred to asCOL-Luc) had a nucleotide sequence comprising a nucleotide sequenceencoding the amino acid sequence of firefly luciferase as a reportergene linked downstream of the nucleotide sequence −3500 to +57 (thetranscription initiation point is +1) of a transcription regulatoryregion for a human-derived Type I collagen α2 chain gene.

Example 23 Measurement of the Ability of a Test Compound to RegulateTranscription of a Type I Collagen Gene Using the Expression Level of aReport Gene as an Index

1×10⁶ cells of a normal human fetal skin fibroblast were seeded on a 100mm dish and cultured at 37° C. overnight under 5% CO₂ atmosphere in aDulbecco's-MEM (Nissui Seiyaku, catalogue No. 05919) medium containing10 (v/v) % heat-inactivated bovine fetal serum (hereinafter, referred toas FBS; Gibco, catalogue No. 21140-079) (hereinafter, this medium isreferred to as D-MEM(+)). Then, the medium was replaced with aDulbecco's-MEM medium not containing FBS (hereinafter, this medium isreferred to as D-MEM(−)).

To 300 μl of D-MEM(−) were added 5 μg of COL-Luc and 5 μg of pCMV-β-gal(Invitrogen, catalogue No. 10586-014), and the resulting mixed solutionwas allowed to stand at room temperature for 5 minutes (solution 1). To300 μl of D-MEM(−) was added 20 μl of Lipofectine (Gibco, catalogue No.18292-011), and the resulting mixed solution was allowed to stand atroom temperature for 45 minutes (solution 2). Then, the solution 1 andthe solution 2 were mixed. After the mixture was allowed to stand atroom temperature for 10 minutes, 5.4 ml of D-MEM(−) was added tothereto, followed by mixing. The mixed solution was added to the normalhuman fetal skin fibroblasts, and the cells were cultured at 37° C.under 5% CO₂ atmosphere. After 6 hours, the culture supernatant wasremoved from the dish, and the cells were washed with PBS twice. To thedish was added 1 ml of PBS containing 0.25% trypsin, and the cells werescraped off the dish. To the scraped cells was added D-MEM(+), and thesewere mixed well. The mixture was dispensed into a 12-well plate at 1 mlper well, and the plate was incubated at 37° C. overnight under 5% CO₂atmosphere. On the next day, each well was washed with D-MEM(−) twice,and this was replaced with 1 ml of a Dulbecco's-MEM medium containing0.1% FBS (hereinafter, this medium is referred to as D-MEM (0.1%)).

To the thus cultured cells was added 10 μl of a 100 μM solution of thepresent compound represented by the compound number (2a-17), (2c-17),(3a-32) or (3c-32) in dimethyl sulfoxide (hereinafter, DMSO) (finalconcentration 1 μM). As a control, only 10 μl of DMSO was added.

After one hour, 10 μl of a 0.5 μg/ml aqueous solution of TGF-β (PeproTech) or distilled water was added to the well, and the plate wasfurther incubated at 37° C. for 40 hours under 5% CO₂ atmosphere. Afterthe incubated cells were washed with PBS twice, 200 μl of a cell lysingagent (Toyo Inc., catalogue No. PD10) was added thereto and the cellswere scraped. The scraped cells were recovered as a cell suspension, andthe suspension was centrifuged (15,000 rpm, 4° C., 5 min) to recover asupernatant. The recovered supernatant was transferred to a 96-wellplate at 50 μl per well, and then 50 μl of a Luc assay solution (20 mMTricine (pH 7.8), 2.67 mM MgSO₄, 0.1 mM EDTA, 33.3 mM DTT, 270 μMCoenzyme A, 530 μM ATP, 470 μM Luciferin) was automatically dispensedinto the plate using MICROLUMAT LB96P (manufactured by EG&G BERTHOLD).Luminescence in each well was measured (Delay: 1.6 second, Meas.Interval: 20 second).

On the other hand, 50 μl of the recovered supernatant or the cell lysingagent was added to 50 μl of a β-gal substrate solution (5.8 mMo-nitrophenyl-beta-D-galactopyranoside, 1 mM MgCl₂, 45 mM2-mercaptoethanol) which had been dispensed into a 96-well plate inadvance, and the plate was incubated at 37° C. for 2 hours. Then, anabsorbance in each well was measured using a microplate reader at 420nm. Based on the resulting value, the transcription activity wascalculated according to the following equation:Transcription activity=[luminescence amount (supernatant-addedsection)−luminescence amount (cell lysing agent-added section)]/[420 nmabsorbance (supernatant-added section)−420 nm absorbance (cell lysingagent-added section)]

Then, based on the calculated transcription activity, an inhibitoryeffect of a test compound on the ability of TGF-β to promotetranscription of a Type I collagen gene was calculated as an inhibitionpercentage according to the following equation:Inhibition percentage=[transcription activity (DMSO and TGF-β-added testsection)−transcription activity (compound and TGF-β-added testsection)]/[transcription activity (DMSO and TGF-β-added testsection)−transcription activity (DMSO and TGF-β non-added testsection)]×100

The inhibition percentages of the present compounds represented by thecompound number (2a-17), (2c-17), (3a-32) and (3c-32) were 70 or more.It was found that these compounds can inhibit the ability of TGF-β topromote transcription of a Type I collagen gene, and then can suppresstranscription of a Type I collagen gene.

Industrial Applicability

According to the present invention, it is possible to develop andprovide a composition which decreases expression of a Type I collagegene in a tissue to induce a reduction in accumulation of collagen andthereby improves tissue fibrosis (i.e. a collagenaccumulation-suppressing agent and a fibrosing disease-treating agent).

Sequence Listing Free Text

-   SEQ ID NO: 1

Oligonucleotide primer designed for amplifying a collagen promoter DNA

-   SEQ ID NO: 2

Oligonucleotide primer designed for amplifying a collagen promoter DNA

-   SEQ ID NO: 3

Oligonucleotide primer designed for detecting a collagen DNA

-   SEQ ID NO: 4

Oligonucleotide primer designed for detecting a collagen DNA

-   SEQ ID NO: 5

Oligonucleotide probe designed for detecting a collagen DNA

The invention claimed is:
 1. A composition comprising a 2(1H)-pyridinonecompound represented by the formula (XVIII):

wherein X_(III)′ represents a C2-C4 alkyl group, or a C1-C4 alkyl groupsubstituted with a halogen atom or a C1-C4 alkoxy group, or a C2-C4alkenyl group, or a C2-C4 alkenyl group, or a C2-C4 alkoxy group, or aR_(I)—S(O)_(I)-group (wherein R_(I) represents a C1-C4 alkyl group, andl represents an integer of 0 to 2), or a cyano group, or a carboxygroup, or a C1-C4 alkoxycarbonyl group, a (R_(II))₂N-group (whereinR_(II) represents a C2-C4 alkyl group), or a R_(I)—CO—NH-group (whereinR_(I) is as defined above), or a R_(I)O—CO—NH-group (wherein R_(I) is asdefined above), or a R_(I)NH—CO—NH-group (wherein R_(I) is as definedabove), or a (R_(I)′)₂N—CO-group (wherein R_(I)′ represents a hydrogenatom or a C1-C4 alkyl group), or a RB-group (wherein B represents anoxygen atom or a sulfur atom, and R represents a C1-C4 alkyl groupsubstituted with a halogen atom), X_(III)″represents a hydrogen atom, ahalogen atom, a C1-C4 alkyl group, or a C1-C4 alkoxy group, m represents1 or 2, when m is 2, X_(III)″'s may be different, and r_(II) and r_(II)′are the same or different, and represent a hydrogen atom or a C1-C4alkyl group; and an inert carrier.
 2. A 2(1H)-pyridinone compoundrepresented by the formula (XVIII):

wherein X_(III)′ represents a C2-C4 alkyl group, or a C1 -C4 alkyl groupsubstituted with a halogen atom or a C1 -C4 alkoxy group, or a C2-C4alkenyl group, or a C2-C4 alkynyl group, or a C2-C4 alkoxy group, or aR_(I)—S(O)₁-group (wherein R_(I) represents a C1 -C4 alkyl group, and lrepresents an integer of 0 to 2), or a cyano group, or a carboxy group,or a C1-C4 alkoxycarbonyl group, a (R_(II))₂N-group (wherein R_(II)represents a C2-C4 alkyl group), or a R_(I)—CO—NH-group (wherein R_(I)is as defined above), or a R_(I)O—CO—NH-group (wherein R_(I) is asdefined above), or a R_(I)NH—CO—NH-group (wherein R_(I) is as definedabove), or a (R_(I)′)₂N—CO-group (wherein R_(I)′ represents a hydrogenatom or a C1 -C4 alkyl group), or a RB-group (wherein B represents anoxygen atom or a sulfur atom, and R represents a C1-C4 alkyl groupsubstituted with a halogen atom), X_(III)″ represents a hydrogen atom, ahalogen atom, a C1-C4 alkyl group, or a C1-C4 alkoxy group, m represents1 or 2, when m is 2, X_(III)″'s may be different, and r_(II) andr_(II′)are the same or different, and represent a hydrogen atom or aC1-C4 alkyl group.
 3. A method for improving tissue fibrosis, whichcomprises administering an effective amount of the composition accordingto claim 1 to a mammal in need thereof.
 4. A method for suppressing theactivity of TGF-β, which comprises administering an effective amount ofthe composition according to claim 1 to a mammal in need thereof.
 5. Amethod for suppressing transcription of a type I collagen gene, whichcomprises administering an effective amount of the composition accordingto claim 1 to a mammal in need thereof
 6. A compound represented by theformula: